通过朱利亚烯烃化反应立体选择性合成Z-卤代烯烃

Stereoselective synthesis of Z alkenyl halides via Julia olefination.

作者信息

Lebrun Marie-Eve, Le Marquand Paul, Berthelette Carl

机构信息

Department of Medicinal Chemistry, Merck Frosst Centre for Therapeutic Research, Post Office Box 1005, Pointe-Claire/Dorval, Québec H9R 4P8, Canada.

出版信息

J Org Chem. 2006 Mar 3;71(5):2009-13. doi: 10.1021/jo052370h.

DOI:10.1021/jo052370h

PMID:16496987

Abstract

Julia olefination between alpha-halomethyl sulfones and a variety of aldehydes afforded alkenyl halides in good to excellent yields with high E/Z stereoselectivities. Sulfones were readily prepared in two or three steps from commercially available reagents in good yields. Optimization revealed that the nature of the solvent, the base, and the additive were crucial to obtain the desired alkenyl halides.

摘要

α-卤代甲基砜与多种醛之间的Julia烯化反应以良好至优异的产率和高E/Z立体选择性得到了卤代烯烃。砜可通过两到三步由市售试剂以良好的产率轻松制备。优化结果表明，溶剂、碱和添加剂的性质对于获得所需的卤代烯烃至关重要。