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Enantioselective Protonation of Silyl Enolates Catalyzed by a Binap⋅AgF Complex
Author(s) -
Yanagisawa Akira,
Touge Taichiro,
Arai Takayoshi
Publication year - 2005
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.200462325
Subject(s) - enantioselective synthesis , protonation , chemistry , silylation , catalysis , dichloromethane , trimethylsilyl , binap , fluoride , methanol , organic chemistry , medicinal chemistry , inorganic chemistry , solvent , ion
Silver lining : A catalytic enantioselective protonation of trimethylsilyl enolates uses a binap/silver( I ) fluoride complex as a chiral catalyst in a mixture of dichloromethane and methanol (see scheme). Various ketones with tertiary asymmetric carbon centers at the α position can be prepared with high enantioselectivities.