Synlett 2015; 26(08): 1111-1115
DOI: 10.1055/s-0034-1380265
letter
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Michael Addition Catalyzed by an Optically Active 1-Chlorovinyl Cobalt(III) Complex

Tatsuyuki Tsubo
Department of Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan   Email: yamada@chem.keio.ac.jp
,
Tohru Yamada*
Department of Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan   Email: yamada@chem.keio.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 17 December 2014

Accepted after revision: 01 February 2015

Publication Date:
09 March 2015 (online)


Abstract

The optically active 1-chlorovinyl cobalt(III) complex was prepared from the ketoiminatocobalt(II) complex upon treatment with sodium borohydride in the presence of 1,1,1-trichloroethane. The obtained complex was found to catalyze the enantioselective Michael addition of various malonates on cyclic or acyclic enones to afford the corresponding adduct. In this reaction, the use of sodium alkoxide as a base with 1-chlorovinyl cobalt(III) complex catalyst was crucial to improving both the reactivity and enantioselectivity.

Supporting Information