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Asymmetric Aldol Reaction Catalyzed by a Chiral Phosphine–Silver Complex
Author(s) -
Yanagisawa Akira,
Miyake Ryoji,
Yoshida Kazuhiro
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402351
Subject(s) - chemistry , aldol reaction , trifluoromethanesulfonate , phosphine , catalysis , optically active , organic chemistry , alkyl , lactone , enantioselective synthesis , methanol , medicinal chemistry , base (topology) , mathematical analysis , mathematics
A catalytic asymmetric aldol reaction of alkenyl trihaloacetates or a γ,δ‐unsaturated δ‐lactone with aldehydes or an α‐keto ester was achieved by using a 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl · silver trifluoromethanesulfonate complex as the chiral precatalyst and N , N ‐diisopropylethylamine as the base precatalyst in the presence of methanol. Optically active α‐alkyl β‐hydroxy ketones with enantioselectivities of up to 95 % ee were diastereoselectively obtained in moderate to high yields through the in situ generated chiral silver enolates.