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Stereoselective Preparation of 1-Siloxy-1-alkenylcopper Species by 1,2-C^sp2-to-O Silyl Migration of Acylsilanes

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Akira Tsubouchi,* Kotaro Onishi, and Takeshi Takeda*

Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan

J. Am. Chem. Soc., 2006, 128 (44), pp 14268–14269

DOI: 10.1021/ja0658822

Publication Date (Web): October 12, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, takeda-t@cc.tuat.ac.jp

Abstract

1-Siloxy-1-alkenylcopper species were generated by 1,2-C^sp2-to-O silyl migration of the copper enolates of acyltriphenylsilanes. The alkenylcopper species reacted with methyl, benzyl, allylic, and tributylstannyl halides to give geometrically pure (Z)-enol silyl ethers. In the presence of Pd(0) catalyst, the cross-coupling of the alkenyl copper species with aryl and alkenyl iodides also proceeded to give the (Z)-enol silyl ethers with high stereoselectivity.

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Published In Issue November 08, 2006
Received August 14, 2006

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Communication

Stereoselective Preparation of 1-Siloxy-1-alkenylcopper Species by 1,2-C^sp2-to-O Silyl Migration of Acylsilanes