Premium
Asymmetric Allylation of Carbonyl Compounds Catalyzed by a Chiral Phosphine–Silver Complex
Author(s) -
Yanagisawa Akira,
Yang Nan,
Bamba Kentaro
Publication year - 2017
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.201701177
Subject(s) - chemistry , phosphine , triethylamine , catalysis , binap , enantioselective synthesis , medicinal chemistry , optically active , organic chemistry
A catalytic, asymmetric allylation reaction of aldehydes or ketones with allyltrimethoxysilane was achieved by using a BINAP · AgBF 4 [BINAP = 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl] complex as the chiral precatalyst and triethylamine as the base precatalyst in the presence of 2,2,2‐trifluoroethanol. Optically active homoallylic alcohols with up to 95 % ee were obtained in moderate to high yields through the in situ generated chiral allyl silver catalyst.