期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 23, 页码 8939-8955出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo902066y
关键词
-
资金
- NSERC (Canada)
- Canada Research Chair Program
- Canada Foundation for Innovation
- Universite de Montreal
- Financiere Manuvie
- J.A. DeSeve Foundation
In this article, we describe our efforts toward the enantioselective formation of 1,1-cyclopropane diesters via the metal-catalyzed cyclopropanation of olefins. The strategies envisioned to achieve Such a goal are discussed as Well as the results that led Lis to the discovery of the powerful trans-directing ability of the amide group in Rh(II)-catalyzed cyclopropanation reactions. We Show how this feature enables a Solution for the stereoselective synthesis of 1,1-dicarboxy cyclopropane derivatives. The scope and limitations are discussed as well as the demonstration that these newly formed cyclopropanes display reactivity similar to that of 1,1-cyclopropane diesters. Conversely, 1, 1-cyclopropane diesters Could be accessed in two steps from commercially available alkenes. The potential utility of this methodology IS illustrated by several functional group transformations and Its use in the expedient stereoselective Formal Synthesis Of (S)-(+)-curcumene, (S)-(+)-nuciferal, (S)-(+)-nuciferol, (+)-erogorgiaene, (+/-)-xanthorrhizol, and (+/-)-2-hydroxycalamenene.
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