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Michael Addition Catalyzed by Chiral Secondary Amine Phosphoramide Using Fluorinated Silyl Enol Ethers: Formation of Quaternary Carbon Stereocenters
Author(s) -
Yu JinSheng,
Liao FuMin,
Gao WeiMing,
Liao Kui,
Zuo RunLin,
Zhou Jian
Publication year - 2015
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.201501747
Subject(s) - stereocenter , silylation , enol , amine gas treating , chemistry , catalysis , quaternary carbon , organic chemistry , michael reaction , carbon fibers , tertiary amine , enantioselective synthesis , materials science , composite number , composite material
A chiral secondary amine phosphoramide was developed and identified as a powerful catalyst for the Mukaiyama–Michael addition of fluorinated enol silyl ethers to tetrasubstituted olefins. The resulting products are obtained with high enantioselectivities and contain a quaternary carbon stereocenter bearing either a difluoroalkyl or monofluoroalkyl group.