Stereoselective preparation of 1-siloxy-1-alkenylcopper species by 1,2-Csp2-to-O silyl migration of acylsilanes |
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Authors: | Tsubouchi Akira Onishi Kotaro Takeda Takeshi |
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Institution: | Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan. |
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Abstract: | 1-Siloxy-1-alkenylcopper species were generated by 1,2-Csp2-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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