Synlett 2013; 24(9): 1155-1159
DOI: 10.1055/s-0033-1338439
letter
© Georg Thieme Verlag Stuttgart · New York

BINAM-mono-PHOS as New Entry for Multinuclear Copper Catalysts in Asymmetric Conjugate Addition of Organozinc Reagents

Kohei Endo*
a   Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa 920-1192, Japan   Email: kendo@se.kanazawa-u.ac.jp
b   PRESTO, Japan Science and Technology Agency (JST), 4-1-8 Honcho Kawaguchi, Saitama 332-0012, Japan
,
Ryotaro Takayama
c   Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan   Fax: (+81)352688098   Email: tshibata@waseda.jp
,
Takanori Shibata*
c   Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan   Fax: (+81)352688098   Email: tshibata@waseda.jp
› Author Affiliations
Further Information

Publication History

Received: 13 March 2013

Accepted after revision: 02 April 2013

Publication Date:
23 April 2013 (online)


Abstract

The readily functionalized ligands, BINAM-PHOS, participate in the copper-catalyzed asymmetric conjugate addition of organozinc reagents to enones. The incorporation of benzoyl derivatives on nitrogen atoms was crucial to promote the reaction. ­Notably, BINAM-PHOS derivatives gave the opposite major enantiomers to that obtained using BINOL-PHOS derivatives, which we have developed for the construction of multinuclear catalysts.

Supporting Information