期刊
CHEMICAL RECORD
卷 7, 期 2, 页码 115-124出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.20113
关键词
remote stereocontrol; diastereoselectivity; allylstannanes; allylgermanes; organobismuth
Alk-2-enyl(trialkyl)stannanes with heteroatom substituents at the 4, 5, and 6-positions are transmetallated stereoselectively using tin(IV) halides to generate allyltin trihalides, which react with aldehydes to give (3Z)-homoallylic alcohols with efficient 15, 1,6-, and 1,7-stereocontrol. This chemistry has been used to develop new strategies for natural product synthesis. Because of the toxicity of organotin reagents' and the problems in removing organotin residues from reaction products, alternative procedures that avoid the use of organotin reagents have been investigated. To date, alk-2-enylgermanium reagents have been shown to deliver effective 1,5- and 1,6-stereocontrol, which is analogous to that observed for the organotin compounds. Organobismuth intermediates, which can be generated from allyl bromides and zinc-bismuth(III) iodide, react with aldehydes with efficient 1,5-stereocontrol which is complementary to that observed with the organo-stannanes or -germanes in that (3E)-homoallylic alcohols are obtained. (c) 2007 The Japan Chemical Journal Forum and Wiley Periodicals, Inc.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据