The highly enantioselective addition of indoles and pyrroles to isatins-derived N-Boc ketimines catalyzed by chiral phosphoric acids
Chemical CommunicationsPublished 1 January 2012Open access
Jingchao Feng, Wenjin Yan, Dong Wang, Peng Li, Quantao Sun, Rui Wang
Citations189
SJR quartileQ1
SJR score1.04
SNIP0.78
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
The first asymmetric aza-Friedel-Crafts reaction of indoles and pyrroles with isatin-derived N-Boc ketimines catalyzed by chiral phosphoric acids is reported, with excellent enantioselectivities and high yields.
Abstract
The first asymmetric aza-Friedel-Crafts reaction of indoles and pyrroles with isatin-derived N-Boc ketimines catalyzed by chiral phosphoric acids is reported. In general, derivatives of substituted 3-amino-2-oxindoles were obtained with excellent enantioselectivities and high yields.
Keywords
ChemistryBiochemistry, Genetics and Molecular BiologyPharmacology, Toxicology and Pharmaceutics
Chemical ReviewsPractical Methodologies for the Synthesis of Indoles
2,121 Citations2006Guy R. Humphrey, Jeffrey T. Kuethe
Chemical ReviewsSynthesis and Functionalization of Indoles Through Palladium-catalyzed Reactions
1,768 Citations2005Sandro Cacchi, Giancarlo Fabrizi
P palladium-catalyzed synthesis can provide access to fine chemicals, agrochemical and pharmaceutical intermediates, and active ingredients in fewer steps and with less waste than classical.
Angewandte Chemie International EditionCatalytic Functionalization of Indoles in a New Dimension
1,421 Citations2009Marco Bandini, Astrid Eichholzer
This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.
SynthesisChiral Phosphoric Acids as Versatile Catalysts for Enantioselective Transformations
1,254 Citations2010Masahiro Terada
ScienceSpiroindolones, a Potent Compound Class for the Treatment of Malaria
1,211 Citations2010Matthias Rottmann, Case W. McNamara +25 more
The preclinical profile for an optimized spiroindolone drug candidate, NITD609, shows pharmacokinetic properties compatible with once-daily oral dosing and has single-dose efficacy in a rodent malaria model.
Chemical CommunicationsBinaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon–carbon bond forming reactions
1,025 Citations2008Masahiro Terada
Binaphthol-derived monophosphoric acids have been designed as novel chiral Brønsted-acid catalysts, which function as efficient enantioselective catalysts for a variety of organic transformations, especially for carbon-carbon bond forming reactions.
Chemical ReviewsCatalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update
964 Citations2011Shu̅ Kobayashi, Yuichiro Mori +2 more
Chemical ReviewsCatalytic Asymmetric Synthesis of α-Amino Acids
812 Citations2007Carmén Nájera, José M. Sansano
Chemical Society ReviewsChiral Brønsted acid catalyzed Friedel–Crafts alkylation reactions
757 Citations2009Shu‐Li You, Quan Cai +1 more
In this tutorial review, recent progress in the development of chiral Brønsted acid-catalyzed asymmetric Friedel-Crafts reactions is presented.
Chemical ReviewsCatalytic Asymmetric Friedel−Crafts Alkylation Reactions—Copper Showed the Way
757 Citations2008Thomas B. Poulsen, Karl Anker Jørgensen
Alkylation with Activated Alkenes and Carbonyl Compounds in Copper Complexes and Other Metal Complexes: The Incubation Period 2904-2904 3.2.1.
Chemical Society ReviewsMulticomponent reactions for the synthesis of pyrroles
720 Citations2010Verónica Estévez, Mercedes Villacampa +1 more
Multicomponent reactions are one of the most interesting concepts in modern synthetic chemistry and provide an attractive entry into pyrrole derivatives, which are very important heterocycles from many points of view.
Chemical ReviewsCyclizations of <i>N</i>-Acyliminium Ions
617 Citations2004Bruce E. Maryanoff, Han‐Cheng Zhang +3 more
Chemical Society ReviewsChiral Brønsted acids in enantioselective carbonyl activations – activation modes and applications
538 Citations2011Magnus Rueping, Alexander Kuenkel +1 more
Different activation modes, key features of the catalysts and the applied substrates are presented and discussed with the goal to elucidate the origin of stereoselectivity in these Brønsted acid catalyzed transformations.
Natural Product ReportsSimple indole alkaloids and those with a nonrearranged monoterpenoid unit
454 Citations2010Minoru Ishikura, Koji Yamada +1 more
Journal of the American Chemical SocietyHighly Enantioselective Friedel−Crafts Reaction of Indoles with Imines by a Chiral Phosphoric Acid
406 Citations2007Qiang Kang, Zhuo‐An Zhao +1 more
Highly enantioselective Friedel−Crafts reactions of indoles with imines catalyzed by a chiral phosphoric acid are developed, affording the 3-indolyl methanamine derivatives with up to >99% ee for a wide range of substrates.
The LancetNon-peptide arginine-vasopressin antagonists: the vaptans
371 Citations2008Guy Decaux, Alain Soupart +1 more
The vaptans are orally and intravenously active non-peptide vasopressin receptor antagonists that are in development and have shown initial positive results in the treatment of Raynaud's disease, dysmenorrhoea, and tocolysis.
Journal of the American Chemical SocietyOrganocatalytic Asymmetric Aza-Friedel−Crafts Alkylation of Furan
353 Citations2004Daisuke Uraguchi, Keiichi Sorimachi +1 more
The present reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion and could be further derivatized to a chiral gamma-butenolid.
Journal of the American Chemical SocietyEnantioselective Friedel−Crafts Reaction of Electron-Rich Alkenes Catalyzed by Chiral Brønsted Acid
331 Citations2006Masahiro Terada, Keiichi Sorimachi
The reaction of various indole derivatives with a broad range of substituted enecarbamates affords the corresponding Friedel−Crafts products in high yield and enantioselectivity.
Angewandte Chemie International EditionChiral Brønsted Acid Catalyzed Enantioselective Friedel–Crafts Reaction of Indoles and α‐Aryl Enamides: Construction of Quaternary Carbon Atoms
321 Citations2007Yi‐Xia Jia, Jun Zhong +3 more
Organic & Biomolecular ChemistryChiral BINOL-derived phosphoric acids: privileged Brønsted acid organocatalysts for C–C bond formation reactions
313 Citations2010Alexandru Zamfir, Sebastian Schenker +2 more
The recent advances have been reviewed in this article with a focus being placed on hydrocyanations, aldol-type, Mannich, Friedel-Crafts, aza-ene- type, Diels-Alder, as well as cascade and multi-component reactions.
Journal of the American Chemical SocietyA Unique Approach to the Concise Synthesis of Highly Optically Active Spirooxazolines and the Discovery of a More Potent Oxindole-Type Phytoalexin Analogue
295 Citations2010Xianxing Jiang, Yiming Cao +4 more
Preliminary biological evaluation of several of the spirooxazolines using a model of acute neuroinflammation revealed promising antipyretic activity and provided an opportunity to discover new antipYretic agents.
Green ChemistryAdvances in catalytic metal-free reductions: from bio-inspired concepts to applications in the organocatalytic synthesis of pharmaceuticals and natural products
295 Citations2011Magnus Rueping, Jérémy Dufour +1 more
This review focuses on recent advances in catalytic metal-free transfer hydrogenations using Hantzsch esters, which are promising and important alternatives to conventional metal- and bio-catalyzed reductions.
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 EditionEnantioselective Michael/Cyclization Reaction Sequence: Scaffold‐Inspired Synthesis of Spirooxindoles with Multiple Stereocenters
261 Citations2011Yiming Cao, Xianxing Jiang +4 more
The process uses a thiourea as chiral organocatalyst and allows the construction of densely functionalized 3,3′-pyrrolidinoyl spirooxindoles with three contiguous stereogenic centers.
Angewandte Chemie International EditionModulating the Acidity: Highly Acidic Brønsted Acids in Asymmetric Catalysis
247 Citations2011Magnus Rueping, Boris J. Nachtsheim +2 more
This Minireview gives an overview of the design and application of these new organocatalysts and presents recent results in this rapidly growing field of chiral highly acidic Brønsted acids.
Angewandte ChemieEnantioselective Michael/Cyclization Reaction Sequence: Scaffold‐Inspired Synthesis of Spirooxindoles with Multiple Stereocenters
237 Citations2011Yiming Cao, Xianxing Jiang +4 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.
Organic LettersThe Highly Enantioselective Addition of Indoles to <i>N</i>-Acyl Imines with Use of a Chiral Phosphoric Acid Catalyst
190 Citations2007Gerald B. Rowland, Emily B. Rowland +3 more
The highly enantioselective organocatalytic addition of N-benzyl indoles to N-acyl imines is reported and attractive features of the reaction include desirable catalyst loadings, good reactivity, generality of substrates, and easily removable groups from both nitrogen atoms.
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.
Chemical CommunicationsSquaramide-catalyzed enantioselective Friedel–Crafts reaction of indoles with imines
175 Citations2010Yong Qian, Gaoyuan Ma +4 more
Chiral squaramides are highly enantioselective catalysts for Friedel-Crafts reaction of indoles with N-tosyl imines, affording 3-indolyl methanamine products in 85- 96% yields and 84-96% ees.
Organic LettersAsymmetric Friedel−Crafts Addition of Indoles to <i>N</i>-Sulfonyl Aldimines: A Simple Approach to Optically Active 3-Indolyl-methanamine Derivatives
167 Citations2006Yi‐Xia Jia, Jian‐Hua Xie +3 more
Chemistry - A European JournalAn Organocatalytic Cascade Strategy for the Enantioselective Construction of Spirocyclopentane Bioxindoles Containing Three Contiguous Stereocenters and Two Spiro Quaternary Centers
163 Citations2012Wangsheng Sun, Gongming Zhu +3 more
A rapid and efficient organocatalytic cascade sequence for the direct construction of spirocyclopentane bioxindoles has been carried out by using a chiral squaramide catalyst in the presence of a base.
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.
Advanced Synthesis & CatalysisAn Easy Entry to Optically Active Spiroindolinones: Chiral Brønsted Acid‐Catalysed Pictet–Spengler Reactions of Isatins
159 Citations2011Sara Duce, Fabio Pesciaioli +6 more
Chemistry - A European JournalHighly Enantioselective Friedel–Crafts Reaction of 4,7‐Dihydroindoles with Imines by Chiral Phosphoric Acids: Facile Access to 2‐Indolyl Methanamine Derivatives
156 Citations2008Qiang Kang, Xiaojian Zheng +1 more
Angewandte Chemie International EditionFacile and Efficient Enantioselective Hydroxyamination Reaction: Synthesis of 3‐Hydroxyamino‐2‐Oxindoles Using Nitrosoarenes
155 Citations2011Ke Shen, Xiaohua Liu +3 more
Advanced Synthesis & CatalysisChiral Phosphoric Acid‐Catalyzed Enantioselective Aza‐Friedel–Crafts Reaction of Indoles
155 Citations2007Masahiro Terada, Shigeko Yokoyama +2 more
Organic LettersOrganocatalytic Enantioselective Friedel−Crafts Reaction of Pyrrole Derivatives with Imines
152 Citations2007Guilong Li, Gerald B. Rowland +2 more
A highly enantioselective Friedel-Crafts reaction of pyrrole derivatives with N-acyl imines catalyzed by chiral phosphoric acids was developed and produced the pyr role derivatives in high yields and enantiOSElectivity.
Chemical CommunicationsAn enantioselective synthesis of heteroaromatic N-tosyl α-amino acids
137 Citations1999Mogens Johannsen
A new synthesis of optically active β-indolyl and pyrrolyl N-tosyl α-amino acids has been developed which uses readily available starting materials and proceeds with a high degree of enantioselection, giving up to 96% enantiomeric purity in 89% yield using 1–5 mol% of a chiral copper(I)–Tol-BINAP catalyst.
Advanced Synthesis & CatalysisAsymmetric Brønsted Acid‐Catalyzed Friedel–Crafts Reactions of Indoles with Cyclic Imines ‐ Efficient Generation of Nitrogen‐Substituted Quaternary Carbon Centers
136 Citations2011Magnus Rueping, Sadiya Raja +1 more
This organocata- lytic reaction provides for the first time optically active indolindolinone derivatives in high yields and with excellent enantioselectivities (up to 91% ee) under mild reaction conditions.
Organic LettersEnantioselective Organocatalytic Synthesis of Quaternary α-Amino Acids Bearing a CF<sub>3</sub> Moiety
129 Citations2011Ralph Husmann, Erli Sugiono +4 more
A highly enantioselective Friedel-Crafts reaction catalyzed by a chiral phosphoric acid was developed and reacted with a wide variety of indole derivatives to afford quaternary α-amino acids in excellent yields and high enantiOSElectivities.
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.
Organic & Biomolecular ChemistryA facile method for the synthesis of oxindole based quaternary α-aminonitriles via the Strecker reaction
122 Citations2010Yun‐Lin Liu, Feng Zhou +4 more
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.
Chemistry & BiologyDivergent Pathways in the Biosynthesis of Bisindole Natural Products
118 Citations2009Katherine S. Ryan, Catherine L. Drennan
These results provide a vantage point for understanding how much of the diversity of the bisindole class is generated from a small number of diverging pathways from L-tryptophan, as well as enabling identification of bisindoles that are likely derived via completely distinct biosynthetic pathways.
Organic LettersHighly Enantioselective Organocatalytic α-Amination Reactions of Aryl Oxindoles: Developing Designer Multifunctional Alkaloid Catalysts
118 Citations2010Tommy Bui, Gloria Hernández‐Torres +2 more
This study provides the first examples of a general organocatalytic method for the creation of nitrogen-containing, tetrasubstituted chiral centers at C(3) of various aryl oxindoles.
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.
Tetrahedron LettersEnantioselective Pictet–Spengler reactions of isatins for the synthesis of spiroindolones
113 Citations2011Joseph J. Badillo, Abel Silva‐Garcia +3 more
A comparison of catalysts provides insight for the substrate scope and factors responsible for efficient catalytic activity and selectivity in the spirocyclization.
Advanced Synthesis & CatalysisCore Scaffold‐Inspired Concise Synthesis of Chiral Spirooxindole‐Pyranopyrimidines with Broad‐Spectrum Anticancer Potency
111 Citations2012Xianxing Jiang, Yulong Sun +7 more
It is found that this new type of spiro alkaloid could inhibit the proliferation of various cancer cells in a preliminary biological evaluation and suggested that spirooxindole-type pyranopyrimidines, developed by an asymmetric Michael/cyclization strategy, can potentially serve as a new kind of anticancer candidate.
Angewandte Chemie International EditionFormation of Optically Active Aromaticα-Amino Acids by Catalytic Enantioselective Addition of Imines to Aromatic Compounds
110 Citations2000Steen Saaby, Xiangming Fang +2 more
Bioorganic & Medicinal Chemistry LettersDesign and synthesis of novel HIV-1 protease inhibitors incorporating oxyindoles as the <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" altimg="si1.gif" overflow="scroll"><mml:mrow><mml:msubsup><mml:mrow><mml:mi mathvariant="normal">P</mml:mi></mml:mrow><mml:mrow><mml:mn>2</mml:mn></mml:mrow><mml:mrow><mml:mo>′</mml:mo></mml:mrow></mml:msubsup></mml:mrow></mml:math>-ligands
106 Citations2006Arun K. Ghosh, Gary E. Schiltz +7 more
A series of novel oxyindole-derived HIV-1 protease inhibitors were designed and synthesized based upon the X-ray crystal structure of inhibitor 2 (TMC-114) bound to HIV- 1 protease and exhibited low nanomolar inhibitory potencies against HIV protease.
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.
Organic LettersDirect Synthesis of Chiral 1,2,3,4-Tetrahydropyrrolo[1,2-<i>a</i>]pyrazines via a Catalytic Asymmetric Intramolecular Aza-Friedel–Crafts Reaction
101 Citations2011Yuwei He, Mao‐Hui Lin +4 more
The direct asymmetric intramolecular aza-Friedel-Crafts reaction of N-aminoethylpyrroles with aldehydes catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines with high yields and high enantioselectivities.
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.
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.
The Journal of Organic ChemistryEnantioselective and Solvent-Controlled Diastereoselective Mannich Reaction of Isatin Imines with Hydroxyacetone: Synthesis of 3-Substituted 3-Aminooxindoles
92 Citations2012Qi‐Xiang Guo, Yu‐wan Liu +3 more
The diastereoselectively switchable enantioselective Mannich reaction of isatin imines with hydroxyacetone with chiral primary amino acid catalyzed to afford both anti- and syn-Mannich adducts in high yields, good diastreoselectivities, and enantiOSElectivities is reported.
The Journal of Organic ChemistryOptically Active Aromatic and Heteroaromatic α-Amino Acids by a One-Pot Catalytic Enantioselective Addition of Aromatic and Heteroaromatic C−H Bonds to α-Imino Esters
92 Citations2002Steen Saaby, Pau Bayón +2 more
The development of a practical one-pot catalytic enantioselective procedure for the synthesis of non-natural aromatic and heteroaromatic alpha-amino acids is reported.
Organic LettersHighly Functional Group Compatible Rh-Catalyzed Addition of Arylboroxines to Activated <i>N</i>-<i>tert</i>-Butanesulfinyl Ketimines
86 Citations2011Hyung Hoon Jung, Andrew W. Buesking +1 more
The rhodium-catalyzed addition of readily accessible arylboroxines to N-tert-butanesulfinyl ketimines derived from oxetan-3-one, N-Boc-azetidin- 3- one, and isatins proceeds in high yields with excellent functional group compatibility.
The Journal of Organic ChemistryChiral Sulfonimide as a Brønsted Acid Organocatalyst for Asymmetric Friedel–Crafts Alkylation of Indoles with Imines
79 Citations2011Ling‐Yan Chen, Hao He +2 more
Binaphthyl-based chiral sulfonimide (CSI) is demonstrated for the first time to be an efficient, strong Brønsted acid in asymmetric organocatalysis.
Tetrahedron LettersOn the mechanism of stereoselection in direct Mannich reaction catalyzed by BINOL-derived phosphoric acids
78 Citations2006Ilya D. Gridnev, Mitsuhiro Kouchi +2 more
Organic LettersOrganocatalytic Enantioselective Friedel−Crafts Reactions of 1-Naphthols with Aldimines
77 Citations2011Guixia Liu, Shilei Zhang +3 more
An organocatalytic enantioselective Friedel-Crafts reaction of 1-naphthols with aldimines has been developed and affords a direct access to chiral aminoarylnaphthol in good yields and with good to high enantiOSElectivities.
European Journal of Organic ChemistryAsymmetric Organocatalytic Aza‐Friedel–Crafts Reaction of Naphthols with <i>N</i>‐Sulfonyl Imines
75 Citations2011Pankaj Chauhan, Swapandeep Singh Chimni
The cupreine-derived bifunctional organocatalyst BzCPN efficiently catalyzes the formation of aza-Friedel–Crafts products in good to excellent yields and with high enantioselectivities under mild reaction conditions, with a low catalyst loading.
Topics in heterocyclic chemistryFunctionalization of Indole and Pyrrole Cores via Michael-Type Additions
69 Citations2007Nurullah Saraçoğlu
The present review focuses only on the functionalization of indoles and the pyrroles via Michael additions because of the potential biological activity exhibited by these compounds.
Advanced Synthesis & CatalysisA Novel Method for Synthesizing N‐Alkoxycarbonyl Aryl α‐Imino Esters and Their Applications in Enantioselective Transformations
62 Citations2012Yu Qian, Changcheng Jing +2 more
A new strategy for the synthesis of N-alkoxycarbonyl aryl α-imino esters in the presence of dirhodium tetraacetate is reported to produce the desired compounds in high yield (up to 96%) under mild reaction conditions.
The Journal of Organic ChemistryZinc-Mediated Diastereoselective Synthesis of 3-Amino Oxindoles by Addition of Methyl and Terminal Alkynes to <i>N</i>-<i>tert</i>-Butanesulfinyl Ketimines
50 Citations2012Wenjin Yan, Dong Wang +3 more
A zinc-mediated addition of methyl and terminal alkynes to chiral N-tert-butanesulfinyl ketimines for the preparation of optical quaternary 3-amino oxindoles was reported, affording the desired products in high yields and good to excellent diastereoselectivities.
Tetrahedron AsymmetryAsymmetric construction of quaternary stereocenters by direct conjugate addition of oxindoles to enone
34 Citations2010Wangsheng Sun, Liang Hong +2 more
Chiral cinchona-based primary amine A was found to catalyze the asymmetric direct conjugate addition of prochiral 3-oxindoles with enones to afford 3,3-disubstituted oxindoles in good yields, moderate to high diastereoselectivity, and excellent enantioselectivities.
Organic LettersStereoselective Synthesis of All Stereoisomers of Orthogonally Protected Cyclobutane-1,2-diamine and Some Chemoselective Transformations
20 Citations2012Marta Sans, Ona Illa +1 more
Orthogonal protection allows the chemoselective manipulation of both amino groups in protected cyclobutane-1,2-diamine.