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Communication | Special issue | Vol 82, No. 2, 2010, pp.1181-1187
Published online, 6th October, 2010
DOI: 10.3987/COM-10-S(E)122
Asymmetric Synthesis of γ-Siloxyenamides via Chiral Auxiliary-Mediated Diastereoselective Coupling of Ynamides, Aldehydes, and Silane by Nickel Catalyst

Nozomi Saito, Tomoyuki Katayama, and Yoshihiro Sato*

*Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

A nickel-catalyzed diastereoselective three-component coupling of optically active oxazolidinone-derived ynamides, aldehydes, and silane is described. The reaction proceeded via stereoselective formation of oxanickelacycle to give γ-siloxyenamide derivatives in a highly diastereoselective manner.