Enantioselective Construction of Vicinal Sulfur‐containing Tetrasubstituted Stereocenters via Organocatalyzed Mannich‐Type Addition of Rhodanines to Isatin Imines
Advanced Synthesis & CatalysisPublished 23 June 2018Open access
Qiuhong Huang, Lili Zhang, Yuyu Cheng, Pengfei Li, Wenjun Li
Citations33
SJR quartileQ1
SJR score0.93
SNIP0.92
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.
Abstract
Abstract The catalyzed enantioselective nucleophilic addition of rhodanines has been established by employing isatin‐derived imines as suitable partners under chiral squaramide catalysis. By using this strategy, the resulting 3‐substituted 3‐amino‐2‐oxindoles featuring both rhodanine and vicinal sulfur‐containing tetrasubstituted stereocenters structural motifs were obtained in high yields with excellent enantioselectivities and diastereoselectivities. magnified image
Keywords
Chemistry
Current Topics in Medicinal ChemistrySulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry
1,954 Citations2016Minghao Feng, Bingqing Tang +2 more
Sulfonamides, thioethers, sulfones and Penicillin are the most common scaffolds in sulfur containing drugs, which are well studied both on synthesis and application during the past decades.
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.
Chemistry - An Asian JournalTransfer of Sulfur: From Simple to Diverse
605 Citations2013Hui Liu, Xuefeng Jiang
This Focus Review collects and summarize the C-S bond-formation reactions that have been used to construct C- S bonds in natural products and pharmaceutical compounds.
Journal of Medicinal ChemistrySpirotetrahydro β-Carbolines (Spiroindolones): A New Class of Potent and Orally Efficacious Compounds for the Treatment of Malaria
425 Citations2010Bryan K. S. Yeung, Bin Zou +22 more
Improvement of the pharmacokinetic profile of the series translated to exceptional oral efficacy in the P. berghei infected malaria mouse model where full cure was achieved in four of five mice with three daily doses of 30 mg/kg.
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.
SynthesisAsymmetric Sulfa<b>-</b>Michael Additions
310 Citations2007Dieter Enders, K. Luttgen +1 more
Current Medicinal ChemistryRhodanine as a Privileged Scaffold in Drug Discovery
271 Citations2009Tihomir Tomašič, Lucíja Peterlin Mašič
Rhodanines, thiazolidine-2,4-diones and pseudothiohydantoins have become a very interesting class of heterocyclic compounds since the introduction of various glitazones and epalrestat into clinical use for the treatment of type II diabetes mellitus and diabetic complications, respectively.
Beilstein Journal of Organic ChemistryAsymmetric synthesis of tertiary thiols and thioethers
195 Citations2011Jonathan Clayden, Paul MacLellan
This review details the most practical of the methods available for the asymmetric synthesis of tertiary thiols and describes their applications in biological and medicinal chemistry.
Organic LettersHighly Enantioselective Addition of Enals to Isatin-Derived Ketimines Catalyzed by N-Heterocyclic Carbenes: Synthesis of Spirocyclic γ-Lactams
195 Citations2012Hui Lv, Bhoopendra Tiwari +3 more
An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities.
Chemical CommunicationsThe highly enantioselective addition of indoles and pyrroles to isatins-derived N-Boc ketimines catalyzed by chiral phosphoric acids
189 Citations2012Jingchao Feng, Wenjin Yan +4 more
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.
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.
Tetrahedron AsymmetryOrganocatalytic asymmetric synthesis of 3-amino-2-oxindole derivatives bearing a tetra-substituted stereocenter
178 Citations2013Pankaj Chauhan, Swapandeep Singh Chimni
Organic LettersSynthesis of <i>N</i>-Alkoxycarbonyl Ketimines Derived from Isatins and Their Application in Enantioselective Synthesis of 3-Aminooxindoles
174 Citations2012Wenjin Yan, Dong Wang +4 more
The enantioselective addition of 1,3-dicarbonyl compounds to this kind of ketimine affords chiral 3-amino oxindoles in high yield and excellent ee.
Angewandte Chemie International EditionPhosphine‐mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates
164 Citations2016Xiaoyu Han, Wai‐Lun Chan +3 more
Journal of the American Chemical SocietyCation Control of Diastereoselectivity in Iridium-Catalyzed Allylic Substitutions. Formation of Enantioenriched Tertiary Alcohols and Thioethers by Allylation of <i>5H</i>-Oxazol-4-ones and <i>5H</i>-Thiazol-4-ones
157 Citations2013Wenyong Chen, John F. Hartwig
The allylation of substituted 5H-oxazol-4-ones provides rapid access to enantioenriched tertiary α-hydroxy acid derivatives unavailable through Mo-catalyzed allylic substitution and provides a novel method to synthesize enantIOen enriched tertiary thiols and thioethers.
Organic LettersBifunctional N-Heterocyclic Carbene-Catalyzed Highly Enantioselective Synthesis of Spirocyclic Oxindolo-β-lactams
144 Citations2014Hanming Zhang, Zhong‐Hua Gao +1 more
The N-heterocyclic carbene-catalyzed Staudinger reaction of ketenes with isatin-derived ketimines was investigated, giving the corresponding spirocyclic oxindolo-β-lactams in high yields with excellent diastereo- and enantioselectivities.
ACS CatalysisCatalytic Enantioselective Construction of Sulfur-Containing Tetrasubstituted Carbon Stereocenters
139 Citations2016Jin‐Sheng Yu, Hongmei Huang +4 more
Angewandte Chemie International EditionOrganocatalytic Asymmetric Addition of Naphthols and Electron‐Rich Phenols to Isatin‐Derived Ketimines: Highly Enantioselective Construction of Tetrasubstituted Stereocenters
138 Citations2015Marc Montesinos‐Magraner, Carlos Vila +5 more
The reaction afforded chiral 3-amino-2-oxindoles with a quaternary stereocenter in high yields with excellent enantioselectivity (up to 99% ee).
Angewandte Chemie International EditionEnantioselective Construction of Vicinal Tetrasubstituted Stereocenters by the Mannich Reaction of Silyl Ketene Imines with Isatin‐Derived Ketimines
135 Citations2014Jiannan Zhao, Bing Fang +5 more
A possible transition state has been proposed to explain the origin of the asymmetric induction and a variety of β-amino nitriles containing congested vicinal tetrasubstituted stereocenters were obtained with excellent outcomes.
Journal of the American Chemical SocietyEnantioselective Construction of Tetrasubstituted Stereogenic Carbons through Brønsted Base Catalyzed Michael Reactions: α′-Hydroxy Enones as Key Enoate Equivalent
132 Citations2014Eider Badiola, Béla Fiser +9 more
It is found that the Michael addition of a range of enolizable carbonyl compounds to α'-oxy enones can afford the corresponding tetrasubstituted carbon stereocenters in high diastereo- and enantioselectivity in the presence of standard BB catalysts.
Angewandte Chemie International EditionEngaging Allene‐Derived Zwitterions in an Unprecedented Mode of Asymmetric [3+2]‐Annulation Reaction
131 Citations2016Muthukumar G. Sankar, M. García-Castro +3 more
The unprecedented annulation reaction successfully facilitated the construction of sp(3) -rich and highly substituted 3,2'-pyrrolidinyl spirooxindoles supporting many chiral centers.
Organic LettersAn Organocatalytic Asymmetric Friedel–Crafts Addition/Fluorination Sequence: Construction of Oxindole–Pyrazolone Conjugates Bearing Vicinal Tetrasubstituted Stereocenters
123 Citations2015Xiaoze Bao, Baomin Wang +5 more
This reaction sequence delivers novel oxindole-pyrazolone adducts featuring vicinal tetrasubstituted stereocenters with a 0.5 mol % catalyst loading in high yield with excellent enantio- and diastereocontrol.
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.
Chemical ScienceHighly enantioselective construction of tertiary thioethers and alcohols via phosphine-catalyzed asymmetric γ-addition reactions of 5H-thiazol-4-ones and 5H-oxazol-4-ones: scope and mechanistic understandings
119 Citations2015Tianli Wang, Zhaoyuan Yu +4 more
ACS CatalysisCatalyst-Controlled Chemoselective and Enantioselective Reactions of Tryptophols with Isatin-Derived Imines
114 Citations2017Fei Jiang, Dan Zhao +4 more
Catalyst-controlled chemoselective and enantioselectives reactions of tryptophols with isatin-derived imines were demonstrated, afforded 3-substituted 3-amino-oxindoles in generally good yields and excellent stereoselectivities.
Organic LettersN-Heterocyclic Carbene-Catalyzed Chemoselective Cross-Aza-Benzoin Reaction of Enals with Isatin-Derived Ketimines: Access to Chiral Quaternary Aminooxindoles
105 Citations2014Jianfeng Xu, Chengli Mou +3 more
A chemo- and enantioselective cross-aza-benzoin reaction between enals and isatin-derived ketimines is disclosed, enabling the high chemoselectivity of the acyl anion reaction over enal α- and β-carbon reactions.
RSC AdvancesStereoselective synthesis of 3-amino-2-oxindoles from isatin imines: new scaffolds for bioactivity evaluation
104 Citations2015Jasneet Kaur, Swapandeep Singh Chimni +2 more
This review focuses on the catalytic asymmetric synthesis of chiral 3-amino-3-substituted-2-oxindoles through the addition of various nucleophiles to isatin imines.
Organic Letters<i>N</i>-Heterocyclic Carbene Catalyzed [4 + 2] Annulation Reactions with in Situ Generated Heterocyclic <i>ortho</i>-Quinodimethanes
100 Citations2016Jianfeng Xu, Shiru Yuan +1 more
The main features of this reaction include challenging direct C(sp(3))-H bond functionalizations, excellent enantioselectivities, readily available starting materials, mild reaction conditions, high efficiency, and operational simplicity.
Organic LettersEnantioselective Organocatalytic 1,6-Addition of Azlactones to <i>para</i>-Quinone Methides: An Access to α,α-Disubstituted and β,β-Diaryl-α-amino acid Esters
95 Citations2018Wenjun Li, Xianhong Xu +4 more
This work describes the first enantioselective 1,6-additions of azlactones to para-quinone methides, and offers a facile synthetic approach, not only to enantiopure α,α-disubstituted α-amino acid esters, but also to unnatural enantioenriched β,β-diaryl-α-aminosacid esters bearing adjacent tertiary and quaternary stereogenic centers.
Angewandte Chemie International EditionStereoselective Organocatalytic Synthesis of Oxindoles with Adjacent Tetrasubstituted Stereocenters
86 Citations2015Oliver D. Engl, Sven P. Fritz +1 more
Oxindoles with adjacent tetrasubstituted stereocenters were obtained in high yields and stereoselectivities by organocatalyzed conjugate addition reactions of monothiomalonates to isatin-derived N-Cbz ketimines.
Angewandte Chemie International EditionChiral Primary Amine Catalysis for Asymmetric Mannich Reactions of Aldehydes with Ketimines: Stereoselectivity and Reactivity
81 Citations2017Jun Dai, Dan Xiong +4 more
These new reactions provide useful methods for the syntheses of chiral 3-substituted 3-amino-2-oxindoles and dihydroquinazolinones bearing a trifluoromethylated quaternary stereocenter.
Organic LettersPd(II)-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatin-Derived Ketimines
80 Citations2015Qun He, Liang Wu +4 more
This asymmetric arylation provides an alternative efficient catalytic method for the preparation of chiral 3-aryl-3-amino-2-oxindoles, which also represents the first example of a Pd(II)-catalyzed addition of arylborons to exocyclic ketimines.
Chemical CommunicationsEnantioselective [2+2] annulation of simple aldehydes with isatin-derived ketimines via oxidative N-heterocyclic carbene catalysis
78 Citations2017Jianfeng Xu, Shiru Yuan +4 more
An asymmetric [2+2] annulation reaction through direct α-carbon functionalization of simple aldehydes via oxidative N-heterocyclic carbene catalysis is disclosed.
European Journal of PharmacologyThe pituitary mediates the anxiolytic-like effects of the vasopressin V1B receptor antagonist, SSR149415, in a social interaction test in rats
75 Citations2006Toshiharu Shimazaki, Michihiko Iijima +1 more
The results suggest that the anxiolytic effects of the vasopressin V(1B) receptor antagonist in the social interaction test are mediated through blockade of the viscous-like substance in the pituitary.
Angewandte Chemie International EditionCatalytic Enantioselective Synthesis of Tertiary Thiols From 5<i>H</i>‐Thiazol‐4‐ones and Nitroolefins: Bifunctional Ureidopeptide‐Based Brønsted Base Catalysis
68 Citations2013Saioa Diosdado, Julen Etxabe +6 more
While many methodologies for the enantiose-lective synthesis of secondary thiols exist, approaches for theasymmetric synthesis offtertiarythiols are clearly necessary to help fill this important gap in organic chemistry.
SynlettA Journey in the Catalytic Synthesis of 3-Substituted 3-Aminooxindoles
68 Citations2015Jian Zhou, Jin‐Sheng Yu +2 more
The efforts in the development of new strategies and reactions for facile access to this prominent framework for efficient construction of 3-Substituted 3-aminooxindoles are described.
Advanced Synthesis & CatalysisRecent Developments in the Stereoselective Synthesis of Nitrogen‐Containing Heterocycles using <i>N</i>‐Acylimines as Reactive Substrates
67 Citations2016Enrico Marcantoni, Marino Petrini
Advanced Synthesis & CatalysisBrønsted Acid‐Catalyzed Enantioselective Synthesis of Isatin‐ Derived <i>N</i>,<i>S</i>‐Acetals
60 Citations2015Christian Beceño, Pankaj Chauhan +3 more
Organic LettersAsymmetric Michael Addition of Substituted Rhodanines to α,β-Unsaturated Ketones Catalyzed by Bulky Primary Amines
58 Citations2012Feng Yu, Haoxiang Hu +2 more
A bulky group was introduced by design into a diamine catalyst, and a series of robust and tunable bulky chiral primary amine catalysts were developed and successfully applied in the direct conjugate addition of substituted rhodanines to α,β-unsaturated ketones.
Chemistry - A European JournalAn Organocatalytic Mannich/Denitration Reaction for the Asymmetric Synthesis of 3‐Ethylacetate‐Substitued 3‐Amino‐2‐Oxindoles: Formal Synthesis of AG‐041R
53 Citations2015Kun Zhao, Tao Shu +3 more
The highly enantioselective organocatalytic addition of ethyl nitroacetate to isatin-derived N-Boc ketimines (Boc = tert-butoxycarbonyl), followed by the removal of the nitro group, is described, which leads to the title compounds as important intermediates of pyrroloindoline alkaloids and related drugs in excellent yields and enantiOSElectivities.
Chemical ScienceAsymmetric [4 + 2] annulation of 5H-thiazol-4-ones with a chiral dipeptide-based Brønsted base catalyst
47 Citations2016Bo Zhu, Shuai Qiu +4 more
A new family of dipeptide-based multifunctional Brønsted base organocatalysts capable of the asymmetric [4 + 2] annulation of 5H-thiazol-4-ones with electron-deficient alkenes is developed.
Bioorganic & Medicinal Chemistry LettersPotent and selective oxindole-based vasopressin 1b receptor antagonists with improved pharmacokinetic properties
46 Citations2011Thorsten Oost, Gisela Backfisch +8 more
A novel series of vasopressin 1b (V1b) receptor antagonists, starting from potent but metabolically labile oxindole SSR149415, resulted in potent and selective V1b receptor antagonists with improved metabolic stability and improved pharmacokinetic properties in rat.
Chemistry - A European JournalUreidopeptide‐Based Brønsted Bases: Design, Synthesis and Application to the Catalytic Enantioselective Synthesis of β‐Amino Nitriles from (Arylsulfonyl)acetonitriles
45 Citations2014Saioa Diosdado, Rosa López +1 more
This work presents a highly efficient organocatalytic methodology for the stereoselective synthesis of β-amino nitriles, in which the key to success is the use of ureidopeptide-based Brønsted base catalysts in combination with (arylsulfonyl)acetonitriles as synthetic equivalents of the acetonitrile anion.
Advanced Synthesis & CatalysisEnantioselective Construction of Cyclic Enaminone‐Based 3‐Substituted 3‐Amino‐2‐oxindole Scaffolds <i>via</i> Catalytic Asymmetric Additions of Isatin‐Derived Imines
44 Citations2016Lujia Zhou, Yu‐Chen Zhang +6 more
This approach will not only offer a useful method for enantioselective construction of the cyclic enaminone-based 3-substituted 3-amino-2-oxindole scaffold, but also enrich the research on catalytic asymmetric addition reactions of isatin-derived imines by using electron-rich olefins as nucleophiles.
Chemistry - A European JournalOrganocatalytic Asymmetric Benzylation and Aldol‐Hemiacetalization of α,β‐Unsaturated Trifluoromethyl Ketones: Efficient Enantioselective Construction of 3,4‐Dihydroisocoumarins
43 Citations2016Jindian Duan, Yuyu Cheng +3 more
A new method has been developed for the organocatalytic enantioselective benzylation and aldol-hemiacetalization of α,β-unsaturated trifluoromethyl ketones with toluene derivatives in the presence of a tertiary amine-thiourea catalyst.
The Journal of Organic ChemistryDipeptide-Based Chiral Tertiary Amine-Catalyzed Asymmetric Conjugate Addition Reactions of 5<i>H</i>-Thiazol/Oxazol-4-Ones
38 Citations2016Jiangtao Li, Shuai Qiu +4 more
A series of valuable N,S- and N,O-containing heterocyclic compounds with excellent enantio- and disastereo-selectivities (up to >99% ee, > 20:1 dr) were attained.
European Journal of Organic ChemistryEnantioselective Organocatalytic Synthesis of Sulfur‐Containing Spirocyclic Compounds
36 Citations2013Pierre‐Yves Géant, Michal Urban +3 more
Two different enantioselective organocatalytic cascade reactions to form new sulfur-containing spirocyclic scaffolds are described, with moderate-to-high selectivities and the use of N-phenylrhodanine as the bis-nucleophile for these reactions also allowed the formation of the corresponding spirocycles adducts.
European Journal of Organic ChemistryEnantioselective Synthesis of Spiro[1,3‐indanedione–tetrahydrothiophene]s by Organocatalytic Sulfa‐Michael/Michael Domino Reaction
35 Citations2015Jindian Duan, Jing Cheng +3 more
The organocatalytic asymmetric domino reaction between 2-arylidene-1,3-indanediones and 4-mercapto-2-butenoates for the construction of chiral spiro skeletons was developed and functionalized chiral Spiro heterocycles were built in one pot in similarly high yields with high asymmetric induction.
Organic & Biomolecular ChemistryOrganocatalytic enantioselective α-amination of 5-substituted rhodanines: an efficient approach to chiral N,S-acetals
32 Citations2014Huanrui Zhang, Baomin Wang +4 more
A highly efficient approach to constructing chiral N,S-acetals using 5-substituted rhodanines as sulfur-bound pronucleophiles catalyzed by natural cinchona alkaloids quinine or quinidine is reported.
Mini-Reviews in Organic ChemistryCatalytic Asymmetric &#945;-Sulfenylation: A New and Efficient Pathway to Access Chiral C-S Bonds
29 Citations2014Xiaowei Zhao, Juan Shen +1 more
Current OrganocatalysisDBU-Catalyzed One-Pot Multicomponent Reaction for the Synthesis of Spirocyclic Tetrahydrothiophene Derivatives
9 Citations2016Jindian Duan, Jing Cheng +1 more
