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Stereocontrolled Creation of All‐Carbon Quaternary Stereocenters by Organocatalytic Conjugate Addition of Oxindoles to Vinyl Sulfone
Author(s) -
Zhu Qiang,
Lu Yixin
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201003837
Subject(s) - stereocenter , enantioselective synthesis , alkyl , catalysis , chemistry , conjugate , thiourea , organic chemistry , aryl , carbon fibers , combinatorial chemistry , materials science , mathematics , mathematical analysis , composite number , composite material
Multifunctional catalysts in operation : A novel class of trifunctional thiourea catalysts containing natural amino acid residues have been prepared (see scheme), and found to be very effective towards the asymmetric addition of 3‐alkyl‐oxindoles to 1,1‐bis(benzenesulfonyl)ethylene. This synthetic protocol has led to the enantioselective synthesis of 3‐alkyl‐3‐aryl‐disubstituted oxindoles and indolines with an all‐carbon quaternary stereogenic center.