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Highly Enantioselective Aldol Reaction with 2‐Trimethylsilyloxyfuran: The First Catalytic Asymmetric Autoinductive Aldol Reaction
Author(s) -
Szlosek Magali,
Figadère Bruno
Publication year - 2000
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/(sici)1521-3773(20000515)39:10<1799::aid-anie1799>3.0.co;2-z
Subject(s) - aldol reaction , enantioselective synthesis , lewis acids and bases , catalysis , lewis acid catalysis , chemistry , organic chemistry , stereochemistry , medicinal chemistry
A stepwise addition of 2‐trimethylsilyloxyfuran (2‐TMSOF) to achiral aldehydes in the presence of a chiral Lewis acid, such as a ( R )‐(1,1′‐bi‐2‐naphthol) 2 Ti complex, affords the corresponding butenolides [Eq. (1)] in good yields with good to excellent ee values (70 to 96 % ee ). This is the first reported catalytic asymmetric autoinductive aldol reaction.