Highly stereoselective addition of stannylcuprates to alkynones

被引：13

作者：

Nielsen, TE ^{[1
]}

de Dios, MAC ^{[1
]}

Tanner, D ^{[1
]}

机构：

[1] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 21期

关键词：

D O I：

10.1021/jo0259008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of stannylcuprate reagents such as (Bu3Sn)(PhS)CuLi to alkynones has been found to proceed in high yield and with excellent stereoselectivity for the Z isomer of the product (>95%). The behavior of the stannylcuprates is thus very different from that of their "carbocuprate" counterparts such as Me2CuLi or Me2Cu(CN)Li-2 which are nonstereoselective. Furthermore, in contrast to the reactions of (R3Sn)(PhS)CuLi with the corresponding alkynoates, the presence of a proton source in the reaction medium has no effect on the stereos electivity of the reaction of alkynones.

引用

页码：7309 / 7313

页数：5

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