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Organocatalytic Asymmetric Conjugate Addition of 2‐Oxindole‐3‐Carboxylate Esters to 2‐Phthalimido Acrylates: Efficient Synthesis of C γ ‐tetrasubstituted α‐Amino Acid Derivatives
Author(s) -
Gao Juan,
Chen JiaRong,
Duan ShuWen,
Li TianRen,
Lu LiangQiu,
Xiao WenJing
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300292
Subject(s) - chemistry , oxindole , thiourea , conjugate , organocatalysis , stereoselectivity , carboxylate , catalysis , enantioselective synthesis , enantiomer , organic chemistry , michael reaction , medicinal chemistry , combinatorial chemistry , mathematical analysis , mathematics
An organocatalytic asymmetric conjugate addition of 2‐oxindole‐3‐carboxylate esters to 2‐phthalimidoacrylates catalyzed by a quinine‐derived thiourea is described. The reaction provides efficient access to a variety of quaternary oxindole based C γ ‐tetrasubstituted α‐amino acid derivatives in good to excellent yields (up to 96 %) with moderate to good enantioselectivity (up to 90 % ee ). The opposite enantiomers of the products can also be obtained with comparable yields and stereoselectivity by simply using a quinidine‐derived thiourea catalyst.