Catalytic Asymmetric Alkylation of Acylsilanes†
Jiawei Rong
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands)
Search for more papers by this authorRik Oost
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands)
Search for more papers by this authorDr. Alaric Desmarchelier
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands)
Search for more papers by this authorProf. Adriaan J. Minnaard
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands)
Search for more papers by this authorCorresponding Author
Prof. Syuzanna R. Harutyunyan
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands)
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands)Search for more papers by this authorJiawei Rong
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands)
Search for more papers by this authorRik Oost
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands)
Search for more papers by this authorDr. Alaric Desmarchelier
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands)
Search for more papers by this authorProf. Adriaan J. Minnaard
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands)
Search for more papers by this authorCorresponding Author
Prof. Syuzanna R. Harutyunyan
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands)
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands)Search for more papers by this authorFinancial support from The Netherlands Organization for Scientific Research (NWO-Vidi, to S.R.H.), the China Scholarship Council (CSC, to J.R.), and the Ministry of Education, Culture and Science (Gravity program 024.001.035) is acknowledged.
Abstract
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.
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