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Catalytic Enantioselective Michael Addition of 1‐Fluorobis(phenylsulfonyl)methane to α,β‐Unsaturated Ketones Catalyzed by Cinchona Alkaloids
Author(s) -
Furukawa Tatsuya,
Shibata Norio,
Mizuta Satoshi,
Nakamura Shuichi,
Toru Takeshi,
Shiro Motoo
Publication year - 2008
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.200802904
Subject(s) - enantioselective synthesis , catalysis , cinchona , chemistry , cinchona alkaloids , michael reaction , organic chemistry , steric effects , salt (chemistry) , adduct , ammonium , conjugate , yield (engineering) , medicinal chemistry , materials science , metallurgy , mathematical analysis , mathematics
A catalyst worth its salt : The ammonium salts of cinchona alkaloids possessing sterically demanding substituents effectively catalyzed the enantioselective 1,4‐conjugate addition of 1‐fluorobis(phenylsulfonyl)methane to α,β‐unsaturated ketones to furnish the Michael adducts in high yield with excellent enantioselectivity (see scheme). The adducts are useful for the synthesis of chiral monofluoromethylated molecules.