Catalytic asymmetric alkylation of acylsilanes.
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.
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands).
Jiawei
J
Rong
Rik
R
Oost
Alaric
A
Desmarchelier
Adriaan J
AJ
Minnaard
Syuzanna R
SR
Harutyunyan
Grignard reactions; acylsilanes; alkylation; asymmetric synthesis; copper catalysis