通过酰基硅烷的1,2-Csp2到O的硅基迁移立体选择性制备1-硅氧基-1-烯基铜物种。
Stereoselective preparation of 1-siloxy-1-alkenylcopper species by 1,2-Csp2-to-O silyl migration of acylsilanes.
作者信息
Tsubouchi Akira, Onishi Kotaro, Takeda Takeshi
机构信息
Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan.
出版信息
J Am Chem Soc. 2006 Nov 8;128(44):14268-9. doi: 10.1021/ja0658822.
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.
通过酰基三苯基硅烷的烯醇铜盐的1,2-Csp2到O的硅基迁移生成1-硅氧基-1-烯基铜物种。该烯基铜物种与甲基、苄基、烯丙基和三丁基锡基卤化物反应，得到几何纯的(Z)-烯醇硅醚。在钯(0)催化剂存在下，烯基铜物种与芳基和烯基碘的交叉偶联反应也能进行，以高立体选择性得到(Z)-烯醇硅醚。
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