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Highly Enantioselective Construction of 3‐Hydroxy Oxindoles through a Decarboxylative Aldol Addition of Trifluoromethyl α‐Fluorinated gem ‐Diols to N ‐Benzyl Isatins
Author(s) -
Saidalimu Ibrayim,
Fang Xiang,
He XiaoPeng,
Liang Jing,
Yang Xueyan,
Wu Fanhong
Publication year - 2013
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.201301443
Subject(s) - aldol reaction , enantioselective synthesis , chemistry , trifluoromethyl , cleavage (geology) , organic chemistry , bond cleavage , medicinal chemistry , catalysis , materials science , alkyl , fracture (geology) , composite material
An organocatalytic asymmetric direct aldol addition reaction that involves cleavage of a carbon–carbon bond through the release of trifluoroacetate was developed. The protocol is wide in scope, generating the desired oxindoles of biological interest in nearly quantitative yields (up to 99 %) with excellent enantioselectivities (up to 98 % ee ) and diastereoselectivities (up to 99:1 d.r.).