A facile method for the synthesis of oxindole based quaternary α-aminonitriles via the Strecker reaction
Organic & Biomolecular ChemistryPublished 1 January 2010
Yun‐Lin Liu, Feng Zhou, Junjie Cao, Cong‐Bin Ji, Miao Ding, Jian Zhou
Citations122
SJR quartileQ2
SJR score0.60
SNIP0.71
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
TL;DR
A new bifunctional cinchona alkaloid-based phosphinamide catalyst 7 could promote the Strecker reaction of isatins derived ketimine with TMSCN in up to 74% ee.
Abstract
The direct alpha-cyanoamination of isatins using TMSCN has been developed, which is carried out in methanol without any catalyst. A new bifunctional cinchona alkaloid-based phosphinamide catalyst 7 could promote the Strecker reaction of isatins derived ketimine with TMSCN in up to 74% ee.
Keywords
ChemistryBiochemistry, Genetics and Molecular Biology
Chemical ReviewsSmall-Molecule H-Bond Donors in Asymmetric Catalysis
2,574 Citations2007Abigail G. Doyle, Eric N. Jacobsen
Angewandte Chemie International EditionPyrrolidinyl‐Spirooxindole Natural Products as Inspirations for the Development of Potential Therapeutic Agents
2,411 Citations2007Chris V. Galliford, Karl A. Scheidt
The 3,3'-pyrrolidinyl-spirooxindole unit is a privileged heterocyclic motif that forms the core of a large family of alkaloid natural products with strong bioactivity profiles and interesting structural properties.
Chemical ReviewsCatalytic Enantioselective Addition to Imines
1,564 Citations1999Shū Kobayashi, Haruro Ishitani
Shū Kobayashi was born in 1959 in Tokyo, Japan and studied chemistry at the University of Tokyo and received his Ph.D. in 1988 (Professor T. Mukaiyama), and received the first Springer Award in Organometallic Chemistry in 1997.
European Journal of Organic ChemistryConstruction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids
1,444 Citations2003Christiane Marti, Erick M. Carreira
Advanced Synthesis & CatalysisCatalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 Position
1,248 Citations2010Feng Zhou, Yun‐Lin Liu +1 more
Chemical Society Reviews(Thio)urea organocatalysis—What can be learnt from anion recognition?
1,093 Citations2009Zhiguo Zhang, Peter R. Schreiner
The present critical review outlines the close relationship and mutual interplay between molecular recognition, active site considerations in enzyme catalysis involving anions, and organocatalysis utilizing explicit hydrogen bonding.
Justus Liebig s Annalen der ChemieUeber die künstliche Bildung der Milchsäure und einen neuen, dem Glycocoll homologen Körper;
1,041 Citations1850Adolph Strecker
Organic LettersHighly Enantioselective Conjugate Addition of Nitromethane to Chalcones Using Bifunctional Cinchona Organocatalysts
979 Citations2005Benedek Vakulya, Szilárd Varga +2 more
Cinchona alkaloid-derived chiral bifunctional thiourea organocatalysts were synthesized and applied in the Michael addition between nitromethane and chalcones with high ee and chemical yields.
Journal of the American Chemical SocietySchiff Base Catalysts for the Asymmetric Strecker Reaction Identified and Optimized from Parallel Synthetic Libraries
895 Citations1998Matthew S. Sigman, Eric N. Jacobsen
ChemInformHighly Enantioselective Conjugate Addition of Nitromethane to Chalcones Using Bifunctional Cinchona Organocatalysts.
816 Citations2005Benedek Vakulya, Szilárd Varga +2 more
Chemical Society ReviewsCombining transition metal catalysis and organocatalysis: a broad new concept for catalysis
802 Citations2009Zhihui Shao, Hongbin Zhang
This critical review of the concept of combining transition metal catalysis and organocatalysis with several recent outstanding examples is illustrated, with the aim of shedding light on the synthetic utilities and potentials of this concept as a novel tool in organic synthesis.
Organic & Biomolecular ChemistryRecognition and activation by ureas and thioureas: stereoselective reactions using ureas and thioureas as hydrogen-bonding donors
761 Citations2005Yoshiji Takemoto
Enantioselective reactions catalyzed by urea and thiourea derivatives as general acid catalysts as well as diastereoselectives reactions are described.
Angewandte Chemie International EditionUrea‐ and Thiourea‐Substituted Cinchona Alkaloid Derivatives as Highly Efficient Bifunctional Organocatalysts for the Asymmetric Addition of Malonate to Nitroalkenes: Inversion of Configuration at C9 Dramatically Improves Catalyst Performance.
660 Citations2005Séamus H. McCooey, Stephen J. Connon
Chemical ReviewsCatalytic Enantioselective Strecker Reactions and Analogous Syntheses
627 Citations2003Harald Gröger
This paper presents the chiral Titanium(IV) Complexes as a Catalyst for Strecker Reaction using Amines, Aldehydes, and HCN for transformation of R-Amino Nitriles into Amino Acid Amides.
Angewandte Chemie International EditionGelsemine: A Thought‐Provoking Target for Total Synthesis
600 Citations2003Hong Lin, Samuel J. Danishefsky
This Review focuses on the comparison of the different strategies to assemble the bicyclo[3.2.1]octane core, to introduce the bridgehead quaternary C20 to form the pyrrolidine moiety, to construct the oxindole residue, and to close the tetrahydropyran ring en route to gelsemine.
Journal of the American Chemical SocietyOrganocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity
572 Citations2009Xiaohua Chen, Qiang Wei +3 more
The straightforward construction of spirooxindole skeletons with high stereo- and regioselectivity suggests a new avenue to medicinal chemistry and diversity-oriented synthesis.
Journal of the American Chemical SocietyStructure-Based Analysis and Optimization of a Highly Enantioselective Catalyst for the Strecker Reaction
571 Citations2002Petr Váchal, Eric N. Jacobsen
Rational optimization of catalyst structure based on the mechanistic insight led to an improved catalyst for the asymmetric Strecker reaction.
Journal of the American Chemical SocietyHighly Enantioselective Conjugate Addition of Malonate and β-Ketoester to Nitroalkenes: Asymmetric C−C Bond Formation with New Bifunctional Organic Catalysts Based on Cinchona Alkaloids
526 Citations2004Hongming Li, Yi Wang +2 more
The development of a new class of readily accessible chiral bifunctional organic catalysts that could be derived in one or two steps in high yield from either quinidine or quinine are described.
Chemical Society ReviewsSome recent applications of α-amino nitrile chemistry
515 Citations2000Dieter Enders, John P. Shilvock
Chemical CommunicationsEnantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives
483 Citations2005Jinxing Ye, Darren J. Dixon +1 more
Thiourea derivative was identified as the most effective bifunctional organic catalyst and found to induce high enantioselectivity in the malonate ester Michael addition reaction to a range of nitro olefins.
Chemistry - An Asian JournalRecent Advances in Multicatalyst Promoted Asymmetric Tandem Reactions
458 Citations2010Jian Zhou
The current achievement of this promising field of multicatalyst promoted asymmetric tandem reactions is discussed, including the advantages and difficulties of this research, and the strategies applied to address these problems.
Natural Product ReportsSimple indole alkaloids and those with a nonrearranged monoterpenoid unit
454 Citations2010Minoru Ishikura, Koji Yamada +1 more
NatureScaleable catalytic asymmetric Strecker syntheses of unnatural α-amino acids
386 Citations2009Stephan J. Zuend, Matthew P. Coughlin +2 more
A new catalytic asymmetric method is reported for the syntheses of highly enantiomerically enriched non-natural amino acids using a simple chiral amido-thiourea catalyst to control the key hydrocyanation step.
Journal of the American Chemical SocietyEnantioselective Bromolactonization of Conjugated (<i>Z</i>)-Enynes
349 Citations2010Wei Zhang, Suqing Zheng +4 more
Preliminary investigations suggest that the chiral catalyst may serve as a bifunctional reagent by interacting with both a carboxylic acid nucleophile and NBS electrophile.
Journal of the American Chemical SocietyCatalytic Enantioselective Fluorination of Oxindoles
344 Citations2005Yoshitaka Hamashima, Toshiaki Suzuki +3 more
In the presence of a catalytic amount of chiral Pd complex 2, various substrates, including aryl- and alkyl-substituted oxindoles, were fluorinated in a highly enantioselective manner, giving a monofluorinated ester with up to 93% ee.
Journal of the American Chemical SocietyThe Mannich Reaction of Malonates with Simple Imines Catalyzed by Bifunctional Cinchona Alkaloids: Enantioselective Synthesis of β-Amino Acids
321 Citations2006Jun Tae Song, Yi Wang +1 more
The first efficient, direct asymmetric Mannich reactions with malonates and N-Boc aryl and alkyl imines by cooperative hydrogen-bonding catalysis with a cinchona alkaloid bearing a thiourea functionality are described.
Angewandte Chemie International EditionRhodium‐Catalyzed Asymmetric Addition of Aryl‐ and Alkenylboronic Acids to Isatins
320 Citations2006Ryo Shintani, Mitsunori Inoue +1 more
Organic LettersEnantioselective Catalytic Addition of HCN to Ketoimines. Catalytic Synthesis of Quaternary Amino Acids
299 Citations2000Petr Váchal, Eric N. Jacobsen
Qu quantitative isolated yield and enantioselectivity of up to 95% ee was obtained and some of the Strecker adducts could be recrystallized in high recovery, yielding optically pure materials.
Journal of the American Chemical SocietyEnantioselective Synthesis of SM-130686 Based on the Development of Asymmetric Cu(I)F Catalysis To Access 2-Oxindoles Containing a Tetrasubstituted Carbon
280 Citations2009Daisuke Tomita, Kenzo Yamatsugu +2 more
An intramolecular catalytic enantioselective arylation of alpha-keto amides was developed, taking advantage of the robustness of arylboronate reagents under multiple synthetic conversions and silica gel column chromatography purification.
SynfactsCatalytic Enantioselective Fluorination of Oxindoles
273 Citations2005Y. Hamashima, T. Suzuki +3 more
Angewandte Chemie International EditionPhosphonium Salts as Chiral Phase‐Transfer Catalysts: Asymmetric Michael and Mannich Reactions of 3‐Aryloxindoles
271 Citations2009Rongjun He, Chang‐Hua Ding +1 more
It's a PTC: A highly efficient reaction of 3-aryloxindoles in an asymmetric Michael addition was achieved by using a quaternary tetraalkylphosphonium salt as a chiral phase-transfer catalyst (PTC).
Journal of the American Chemical SocietyLewis Acid-Catalyzed Enantioselective Hydroxylation Reactions of Oxindoles and β-Keto Esters Using DBFOX Ligand
267 Citations2006Takehisa Ishimaru, Norio Shibata +4 more
The first catalytic enantioselective hydroxylation reaction of both 3-aryl and 3-alkyl-2-oxindoles using the DBFOX-Zn(II) complex, leading to pharmaceutically important chiral 3-hydroxy- 2-Oxindoles was described.
Journal of the American Chemical SocietyCatalytic Asymmetric Synthesis of 3-Aminooxindoles: Enantiofacial Selectivity Switch in Bimetallic vs Monometallic Schiff Base Catalysis
265 Citations2010Shinsuke Mouri, Zhihua Chen +4 more
A highly enantioselective catalytic asymmetric access to 3-aminooxindoles with a tetrasubstituted carbon stereocenter and transformation of the products into an optically active oxindole with a spiro-beta-lactam unit and a known key intermediate for AG-041R synthesis is described.
Angewandte Chemie International EditionBulky Chiral Carbene Ligands and Their Application in the Palladium‐Catalyzed Asymmetric Intramolecular α‐Arylation of Amides
264 Citations2007E. Peter Kündig, Thomas M. Seidel +2 more
New, C2-symmetric bulky N-heterocyclic carbene ligands bring major improvements in the palladium-catalyzed asymmetric intramolecular α-arylation of amides to give oxindoles, which are formed in high yield and excellent enantiomeric purity.
Angewandte Chemie International EditionRecent Developments in Catalytic Asymmetric Strecker-Type Reactions
251 Citations2001Larry Yet
Journal of the American Chemical SocietyCascade Michael−Aldol Reactions Promoted by Hydrogen Bonding Mediated Catalysis
242 Citations2007Liansuo Zu, Jian Wang +4 more
Highly enantio- and diastereoselective tandem Michael−aldol reactions, efficiently catalyzed by a cinchona alkaloid thiourea via synergistic noncovalent hydrogen-bonding activation of both the Michael donor and acceptor, have been developed.
Journal of the American Chemical SocietyIBiox[(−)-menthyl]: A Sterically Demanding Chiral NHC Ligand
227 Citations2009Sebastian Würtz, Claudia Lohre +3 more
An exceedingly sterically demanding, rigid, and chiral NHC ligand was prepared and structurally characterized, and the ability to use aryl chloride substrates in intramolecular palladium-catalyzed alpha-arylations reveals its unique reactivity.
CNS Drug ReviewsBMS‐204352: A Potassium Channel Opener Developed for the Treatment of Stroke
222 Citations2002Bo Jensen
BMS-204352 failed to show superior efficacy in acute stroke patients compared to placebo in a Phase III study that included 1978 patients at 200 centers worldwide, and no clinically significant differences in organ toxicity or adverse effects were found, and total clearance and volume of distribution were independent of dose.
Natural Product ReportsSimple indole alkaloids and those with a nonrearranged monoterpenoid unit (1999)
222 Citations2001Satoshi Hibino, Tominari Choshi
Chemical CommunicationsChiral N-heterocyclic carbene ligands for asymmetric catalytic oxindole synthesis
219 Citations2008Yi‐Xia Jia, J. Mikael Hillgren +3 more
Angewandte Chemie International EditionA Highly Enantioselective Brønsted Acid Catalyst for the Strecker Reaction
210 Citations2006Magnus Rueping, Erli Sugiono +1 more
Journal of the American Chemical SocietyCatalytic Enantioselective Strecker Reaction of Ketoimines
208 Citations2003Shuji Masumoto, Hiroyuki Usuda +3 more
The reaction has a broad substrate generality, giving high enantioselectivity from aromatic, ethyl, primary alkyl, and alpha,beta-unsaturated ketoimines, and could be easily converted to disubstituted alpha-amino acids and their derivatives.
Journal of the American Chemical SocietyCatalytic Asymmetric Strecker Synthesis. Preparation of Enantiomerically Pure α-Amino Acid Derivatives from Aldimines and Tributyltin Cyanide or Achiral Aldehydes, Amines, and Hydrogen Cyanide Using a Chiral Zirconium Catalyst
207 Citations2000Haruro Ishitani, Susumu Komiyama +2 more
The three-component asymmetric process reported here significantly improves upon the original Strecker reaction, and has advantages over previous reactions using unstable imines (Schiff bases) as starting materials.
Angewandte Chemie International EditionProtonated Chiral Catalysts: Versatile Tools for Asymmetric Synthesis
205 Citations2005Carsten Bolm, Toni Rantanen +2 more
Journal of the American Chemical SocietyCatalytic Asymmetric Synthesis of Quaternary Carbons Bearing Two Aryl Substituents. Enantioselective Synthesis of 3-Alkyl-3-Aryl Oxindoles by Catalytic Asymmetric Intramolecular Heck Reactions
205 Citations2003Amy B. Dounay, Keiko Hatanaka +5 more
A practical sequence involving three consecutive palladium(0)-catalyzed reactions has been developed for synthesizing 3-alkyl-3-aryloxindoles in high enantiopurity and a wide variety of aryl and heteroaryl substituents, including ones of considerable steric bulk, can be introduced at C3 of oxindoles.
Angewandte Chemie International EditionA Catalytic Asymmetric Strecker-Type Reaction: Interesting Reactivity Difference between TMSCN and HCN
198 Citations2000Masahiro Takamura, Yoshitaka Hamashima +3 more
Organic LettersHighly Enantioselective and Organocatalytic α-Amination of 2-Oxindoles
193 Citations2009Liang Cheng, Li Liu +2 more
An effective method for the asymmetric synthesis of 3-amino-2-oxindoles with azodicarboxylate catalyzed by commercial biscinchona alkaloids in good to excellent yields with high enantioselectivities.
Journal of the American Chemical SocietyCatalytic Asymmetric Conjugate Addition of Simple Alkyl Thiols to α,β-Unsaturated<i>N</i>-Acylated Oxazolidin-2-ones with Bifunctional Catalysts
191 Citations2008Yan Liu, Bingfeng Sun +3 more
An unprecedented highly enantioselective catalytic conjugate addition of simple alkyl thiols to alpha,beta-unsaturated N-acylated oxazolidin-2-ones catalyzed by acid-base bifunctional catalysis is described.
Organic LettersHighly Enantioselective Amination of α-Substituted α-Cyanoacetates with Chiral Catalysts Accessible from Both Quinine and Quinidine
187 Citations2004Xiaofeng Liu, Hongming Li +1 more
The use of 6‘-OH-modified cinchona alkaloids that are accessible from either quinine or quinidine for the development of a highly enantioselective amination of α,α-disubstituted carbonyl compounds that is suitable for the creation of nitrogen-substituting quaternary stereocenters in either the R or S configuration is described.
Journal of the American Chemical SocietyEnantioselective Diels−Alder Reaction of Simple α,β-Unsaturated Ketones with a Cinchona Alkaloid Catalyst
186 Citations2008Ravi P. Singh, Keith J. Bartelson +4 more
An unprecedented asymmetric Diels−Alder reaction of simple α,β-unsaturated ketones with 2-pyrones has been successfully developed and provides a direct and versatile asymmetric access to a wide range of structurally novel bicyclic chiral building blocks amenable for further synthetic elaborations.
Biochemical and Biophysical Research CommunicationsAG-041R, a Gastrin/CCK-B Antagonist, Stimulates Chondrocyte Proliferation and Metabolism in Vitro
181 Citations2001Mitsuo Ochi, Kenzo Kawasaki +3 more
It is suggested that adequate concentrations of AG-041R stimulate proliferation of chondrocytes in the matrix, without changing their differentiated characteristics, as a potentially effective reagent for the repair of articular cartilage defects.
Journal of the American Chemical SocietyHydrogen-Bond-Promoted Hetero-Diels−Alder Reactions of Unactivated Ketones
179 Citations2002Yong Huang, Viresh H. Rawal
This activation protocol represents an attractive and operationally simple alternative to conventional, Lewis acid catalysis and the use of such catalysis for the hetero-Diels-Alder reactions of simple, unactivated ketones is reported.
Organic LettersOrganocatalytic Stereoselective Mannich Reaction of 3-Substituted Oxindoles
169 Citations2008Xu Tian, Kun Jiang +3 more
The asymmetric Mannich reaction of 3-substituted oxindoles and N-Boc imines was investigated for the first time, employing bifunctional thiourea-tertiary amine organocatalysts based on DPEN scaffold and obtained in good to excellent enantioselectivities.
Angewandte Chemie International EditionA Highly Reactive and Enantioselective Bifunctional Organocatalyst for the Methanolytic Desymmetrization of Cyclic Anhydrides: Prevention of Catalyst Aggregation
163 Citations2008Sang Ho Oh, Ho Sik Rho +5 more
Chemical CommunicationsAsymmetric construction of quaternary stereocenters by direct organocatalytic amination of 3-substituted oxindoles
161 Citations2009Ziqing Qian, Feng Zhou +5 more
Quinidine derivative (QD)(2)PYR was found to catalyze the asymmetric direct amination of unprotected prochiral 3-oxindole with DIAD to construct quaternary stereocenters at the C3 position with excellent enantioselectivity.
Journal of the American Chemical SocietyDimeric Quinidine-Catalyzed Enantioselective Aminooxygenation of Oxindoles: An Organocatalytic Approach to 3-Hydroxyoxindole Derivatives
161 Citations2010Tommy Bui, Nuno R. Candeias +1 more
These reactions allow one to construct a C-O bond at the C(3) position of oxindoles with the creation of an oxygen-containing tetrasubstituted chiral center and provide a new, general organocatalytic approach to the synthesis of 3-hydroxyoxindole derivatives.
Journal of the American Chemical SocietyAsymmetric Strecker Reaction of Aldimines Using Aqueous Potassium Cyanide by Phase-Transfer Catalysis of Chiral Quaternary Ammonium Salts with a Tetranaphthyl Backbone
156 Citations2006Takashi Ooi, Yukitaka Uematsu +1 more
This study represents a novel approach for the asymmetric Strecker-type reactions, which utilizes chiral phase-transfer catalysts for practical access to various unusual, optically pure alpha-amino acids.
The Journal of Organic Chemistry<i>Epi</i>-Cinchona Based Thiourea Organocatalyst Family as an Efficient Asymmetric Michael Addition Promoter: Enantioselective Conjugate Addition of Nitroalkanes to Chalcones and α,β-Unsaturated <i>N</i>-Acylpyrroles
153 Citations2008Benedek Vakulya, Szilárd Varga +1 more
A small set of easily available epi-cinchona based thiourea organocatalysts have been synthesized and tested in enantioselective addition of nitroalkanes to chalcones, and the extension of this methodology was further explored to encompass alpha,beta-unsaturated N-acylpyrroles, as a chalcone mimic.
TetrahedronOrganocatalyzed Strecker reactions
151 Citations2008Pedro Merino, Eugenia Marqués‐López +2 more
Current Organic ChemistryRecent Advances in Catalytic Asymmetric Addition to Imines and Related C=N Systems
150 Citations2005Tirayut Vilaivan, Worawan Bhanthumnavin +1 more
Angewandte Chemie International EditionCatalytic Asymmetric Acylcyanation of Imines
146 Citations2006Subhas Chandra Pan, Jian Zhou +1 more
Angewandte Chemie International EditionRecent Developments in the Catalytic Asymmetric Cyanation of Ketimines
143 Citations2004Claude Spino
Organic LettersAsymmetric Michael Addition Mediated by Novel Cinchona Alkaloid-Derived Bifunctional Catalysts Containing Sulfonamides
143 Citations2008Jie Luo, Li‐Wen Xu +2 more
Novel cinchona alkaloid-derived bifunctional organocatalysts containing sulfonamide groups were utilized to promote Michael addition of bicyclic alpha-substituted beta-ketoesters to nitroolefins, demonstratingThe desired Michael adducts with all-carbon quaternary centers were constructed in high yield and with excellent enantioselectivity.
Chemistry - A European JournalDual Organocatalysis: Asymmetric Allylic–Allylic Alkylation of α,α‐Dicyanoalkenes and Morita–Baylis–Hillman Carbonates
140 Citations2009Hai‐Lei Cui, Jing Peng +4 more
The first highly enantioselective allylic-allylic alkylation of alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman carbonates by dual catalysis of (DHQD)(2)AQN and (S)-BINOL has been investigated.
Advanced Synthesis & CatalysisMetal‐Free, Enantioselective Strecker Reactions Catalyzed by Chiral BINOL and TADDOL Catalysts
135 Citations2007Magnus Rueping, Erli Sugiono +1 more
It is demonstrated that chiral diols, such as TADDOL, are effective enantioselective catalysts for the hydrogen-bond activation of aldimines.
Tetrahedron LettersLithium perchlorate/ diethylether catalyzed aminocyanation of aldehydes
134 Citations1998Akbar Heydari, Parinaz Fatemi +1 more
Tetrahedron LettersFacile and highly stereoselective allylation of aldehydes using allyltrichlorosilanes in DMF
133 Citations1993Shū Kobayashi, Koichi Nishio
Tetrahedron LettersBismuth trichloride catalyzed synthesis of α-aminonitriles
133 Citations2004Surya K. De, Richard A. Gibbs
Angewandte Chemie International EditionThe Catalytic Asymmetric Strecker Reaction: Ketimines Continue to Join the Fold
131 Citations2008Stephen J. Connon
Angewandte Chemie International EditionAsymmetric Activation of <i>tropos</i> 2,2′‐Biphenol with Cinchonine Generates an Effective Catalyst for the Asymmetric Strecker Reaction of <i>N</i>‐Tosyl‐Protected Aldimines and Ketoimines
127 Citations2007Jun Wang, Xiaolei Hu +5 more
Organic LettersAcid-Free Aza Diels−Alder Reaction of Danishefsky's Diene with Imines
124 Citations2002Yu Yuan, Xin Li +1 more
A highly efficient aza Diels-Alder reaction of Danishefsky's diene with imines was found to occur in methanol in the absence of any acids at room temperature to give corresponding 2-substituted dihydro-4-pyridone derivatives in high yields.
British Journal of PharmacologyVasotocin and vasopressin stimulation of the chloride secretion in the human bronchial epithelial cell line, 16HBE14o‐
122 Citations2005Karen Bernard, Stéphanie Bogliolo +1 more
Results point to the stimulation of a V1‐like receptor mediating Ipeak and presenting an efficacy order, AVT>oxytocin>isotocin≫AVP, suggesting the involvement of V2 receptors in the AVP‐induced Iplateau.
The Journal of Organic ChemistryHighly Enantioselective Organocatalytic Sulfa-Michael Addition to α,β-Unsaturated Ketones
121 Citations2010Nirmal K. Rana, Sermadurai Selvakumar +1 more
A cinchona alkaloid-derived urea was found to be an efficient organocatalyst for catalyzing enantioselective conjugate addition between thiols and various alpha,beta-unsaturated ketones to provide optically active sulfides with high chemical yields and enantiomeric excess.
Organic LettersNew Type of Trimeric and Pentameric Indole Alkaloids from <i>Psychotria </i><i>r</i><i>ostrata</i>
120 Citations2004Hiromitsu Takayama, Ikue Mori +3 more
Two new tryptamine-related alkaloids, psychotrimine and psychopentamine, were isolated from the leaves of Psychotria rostrata, and their novel structures were elucidated on the basis of spectroscopic analyses.
The Journal of Organic ChemistryExpanding the Scope of Cinchona Alkaloid-Catalyzed Enantioselective α-Aminations of Oxindoles: A Versatile Approach to Optically Active 3-Amino-2-oxindole Derivatives
118 Citations2009Tommy Bui, Mar Borregán +1 more
A cinchona alkaloid-catalyzed, highly enantioselective, alpha-amination of oxindoles has been developed, which provides a general catalytic method for the construction of a C-N bond at the C3 position of Oxindoles as well as for the creation of a nitrogen-containing, tetrasubstituted chiral center.
Organic LettersA New Chiral Catalyst for the Enantioselective Strecker Synthesis of α-Amino Acids
115 Citations2004Jinkun Huang, E. J. Corey
The chiral ammonium salt 3 is demonstrated to be an effective catalyst for the highly enantioselective Strecker reaction of N-allylbenzaldimines with hydrogen cyanide in CH2Cl2 solution.
The Journal of Organic ChemistryAlkylsilyl cyanides as silylating agents
114 Citations1986Khuong Mai, Ghanshyam Patil
Journal of the American Chemical SocietyDual-Activation Asymmetric Strecker Reaction of Aldimines and Ketimines Catalyzed by a Tethered Bis(8-quinolinolato) Aluminum Complex
112 Citations2009Joshua P. Abell, Hisashi Yamamoto
Organic LettersMatching the Chirality of Monodentate N-Heterocyclic Carbene Ligands: A Case Study on Well-Defined Palladium Complexes for the Asymmetric α-Arylation of Amides
112 Citations2008Xinjun Luan, Ronaldo Mariz +5 more
N-Heterocyclic carbene ligands derived from C(2)-symmetric diamines with naphthyl side chains are introduced as chiral monodentate ligands, and the palladium complexes can be successfully separated and their absolute stereochemistry assigned.
Tetrahedron LettersGeneral and practical catalytic enantioselective Strecker reaction of ketoimines: significant improvement through catalyst tuning by protic additives
111 Citations2004Nobuki Kato, Masato Suzuki +2 more
Organic LettersFacile and General Synthesis of Quaternary 3-Aminooxindoles
111 Citations2008Stephen P. Marsden, Emma Watson +1 more
Chemistry - A European JournalHighly Enantioselective Synthesis of 3‐Amino‐2‐oxindole Derivatives: Catalytic Asymmetric α‐Amination of 3‐Substituted 2‐Oxindoles with a Chiral Scandium Complex
106 Citations2010Zhigang Yang, Zhen Wang +6 more
A highly enantioselective alpha-amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf)(3)/N,N'-dioxide complex (Tf: triflate) has been developed and affords the corresponding 3-amino-2-oxindole derivatives in high yields with excellent enantiOSElectivities.
Chemistry - A European JournalFacile and Efficient Enantioselective Strecker Reaction of Ketimines by Chiral Sodium Phosphate
104 Citations2009Ke Shen, Xiaohua Liu +3 more
A facile and efficient enantioselective Strecker reaction of ketimines catalyzed by a chiral alkali-metal salt has been developed and trimethylsilyl cyanide was indicated to be the real reactive nucleophile despite the existence of PBAP and a possible working model was proposed to explain the origin of the asymmetric induction.
Organic LettersHighly Chemo- and Enantioselective Synthesis of 3-Allyl-3-aryl Oxindoles via the Direct Palladium-Catalyzed α-Arylation of Amides
103 Citations2010Xinjun Luan, Linglin Wu +4 more
A new NHC x Pd-catalyzed asymmetric alpha-arylation of amides is reported that gives direct access to synthetically valuable, allylated oxindoles with quaternary carbon centers.
Advanced Synthesis & CatalysisFacile Creation of 3‐Indolyl‐3‐hydroxy‐2‐oxindoles by an Organocatalytic Enantioselective Friedel–Crafts Reaction of Indoles with Isatins
102 Citations2010Jing Deng, Shilei Zhang +4 more
The first direct enantioselective Friedel-Crafts reaction of indoles with isatins has been developed and affords synthetically and biologically interesting, chiral 3-indolyl-3-hydroxy-2-oxindoles in good yields and with high enantiOSElectivities.
Journal of the American Chemical SocietyMarine alkaloids. 10. Chartelline A: a pentahalogenated alkaloid from the marine bryozoan Chartella papyracea
102 Citations1985Lionel Chevolot, Anne Marie Chevolot +4 more
Chemistry - A European JournalAsymmetric Cyanation of Aldehydes, Ketones, Aldimines, and Ketimines Catalyzed by a Versatile Catalyst Generated from Cinchona Alkaloid, Achiral Substituted 2,2′‐Biphenol and Tetraisopropyl Titanate
101 Citations2009Jun Wang, Wentao Wang +6 more
CNCOOEt was successfully employed for the first time in the asymmetric Strecker reaction of aldimines and ketimines, affording various alpha-amino nitriles with excellent yields and ee values (up to > 99% yield and >99% ee).
Tetrahedron AsymmetrySc(BINOL)2Li: a new heterobimetallic catalyst for the asymmetric Strecker reaction
101 Citations2001Murielle Chavarot, Janice J. Byrne +2 more
Proceedings of the National Academy of SciencesGallium (III) triflate catalyzed efficient Strecker reaction of ketones and their fluorinated analogs
100 Citations2007G. K. Surya Prakash, Thomas Mathew +5 more
Study with various fluorinated and nonfluorinated ketones reveals that the choice of proper catalyst and the solvent system plays the key role in the direct Strecker reactions of ketones.
The Journal of Organic ChemistryEfficient Asymmetric Synthesis of Novel Gastrin Receptor Antagonist AG-041R via Highly Stereoselective Alkylation of Oxindole Enolates
99 Citations2006Takashi Emura, Toru Esaki +2 more
An efficient method for asymmetric synthesis of the potent Gastrin/CCK-B receptor antagonist AG-041R was developed and core oxindole stereochemistry was established by asymmetric alkylation of oxindoles enolates with bromoacetic acid esters, using l-menthol as a chiral auxiliary.
Advanced Synthesis & CatalysisNeutral Coordinate‐Organocatalysts in Organic Synthesis: Allylation of Acylhydrazones with Allyltrichlorosilanes
96 Citations2004Shū Kobayashi, Masaharu Sugiura +1 more
The Journal of Organic ChemistryGrignard Addition to Imines Derived from Isatine: A Method for the Asymmetric Synthesis of Quaternary 3-Aminooxindoles
96 Citations2009Giordano Lesma, Nicola Landoni +3 more
Addition of Grignard reagents to chiral imines derived from isatine afforded chiral, optically enriched 3-substituted 3-aminooxindoles in satisfactory yields and diastereoisomeric ratios.
StressFunctional and Pharmacological Characterization of the First Specific Agonist and Antagonist for the V1b Receptor in Mammals
92 Citations2003Serradeil-Le Gal Claudine, Derick Sylvain +6 more
Interestingly, SSR149415 displays potent anxiolytic and antidepressant-like activities, indicating that this new class of drugs has a promising therapeutical potential in the treatment of stress-related disorders, anxiety and depression.
Chemistry - A European JournalEdge‐to‐Face CH/π Aromatic Interaction and Molecular Self‐Recognition in <i>epi</i>‐Cinchona‐Based Bifunctional Thiourea Organocatalysis
90 Citations2008Gábor Tárkányi, P. Király +3 more
The impact of cooperativity between intermolecular interactions is demonstrated by the molecular self-recognition properties of highly enantioselective epi-cinchona bifunctional thiourea organocatalysts.
European Journal of Organic ChemistryNaproxen Derivatives by Enantioselective Decarboxylation
90 Citations2000Henri Brunner, Péter Schmidt
Chemistry - A European JournalCatalytic Double Stereoinduction in Asymmetric Allylic Alkylation of Oxindoles
84 Citations2009Barry M. Trost, Yong Zhang
A highly regio-, diastereo-, and enantioselective allylic alkylation reaction of 3-monosubstituted oxindoles catalyzed by molybdenum is described and products from this reaction are valuable synthetic intermediates and should find utility in alkaloid synthesis.
Tetrahedron LettersCatalyst-free multicomponent Strecker reaction in acetonitrile
81 Citations2005Ricardo Martínez, Diego J. Ramón +1 more
Organic & Biomolecular ChemistryNovel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency
80 Citations2010Jia‐Rong Chen, Yi‐Ju Cao +5 more
The catalyst 3a, prepared from L-proline and cinchonidine, was found to be a highly efficient catalyst for the conjugate addition of ketones/aldehydes to a wide range of nitroalkenes.
The Journal of Organic ChemistryRational Combination of Two Privileged Chiral Backbones: Highly Efficient Organocatalysts for Asymmetric Direct Aldol Reactions between Aromatic Aldehydes and Acylic Ketones
80 Citations2008Jia‐Rong Chen, Xiao‐Lei An +3 more
The chiral amine 3a, prepared from l-proline and cinchonidine, has been found to be an efficient catalyst for the direct aldol reactions of acetone or 2-butanone with a wide range of aldehydes.
…