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Catalytic Asymmetric Alkylation of Acylsilanes
Author(s) -
Rong Jiawei,
Oost Rik,
Desmarchelier Alaric,
Minnaard Adriaan J.,
Harutyunyan Syuzanna R.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201409815
Subject(s) - chemistry , catalysis , enantioselective synthesis , alkylation , reagent , yield (engineering) , enantiomer , copper , lewis acids and bases , organic chemistry , enantiomeric excess , combinatorial chemistry , medicinal chemistry , materials science , metallurgy
The highly enantioselective addition of Grignard reagents to acylsilanes is catalyzed by copper diphosphine complexes. This transformation affords α‐silylated tertiary alcohols in up to 97 % yield and 98:2 enantiomeric ratio. The competing Meerwein–Ponndorf–Verley reduction is suppressed by the use of a mixture of Lewis acid additives. The chiral catalyst can be recovered as a copper complex and used repeatedly without any loss of catalytic activity.