Li Hongming, Song Jun, Liu Xiaofeng, Deng Li
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
J Am Chem Soc. 2005 Jun 29;127(25):8948-9. doi: 10.1021/ja0511063.
In this communication, we describe the development of the first highly enantioselective catalytic conjugate addition to vinyl sulfones. Promoted by readily accessible organocatalysts derived from C6'-OH cinchona alkaloid derivatives and under mild, air- and moisture-tolerant conditions, conjugate additions of a wide range of alpha-cyanoacetates bearing either an alpha-aryl or an alpha-alkyl substituent to vinyl sulfones proceeded in excellent enantioselectivity and high yield. Consequently, this efficient and operationally simple enantioselective C-C bond forming conjugate addition provides a new and useful approach for the enantioselective construction of all-carbon quaternary stereocenters.
在本通讯中，我们描述了首例对乙烯基砜的高度对映选择性催化共轭加成反应的开发。该反应由易于获得的源自C6'-OH金鸡纳生物碱衍生物的有机催化剂促进，在温和、耐空气和耐湿气的条件下，一系列带有α-芳基或α-烷基取代基的α-氰基乙酸酯与乙烯基砜的共轭加成反应以优异的对映选择性和高产率进行。因此，这种高效且操作简单的对映选择性C-C键形成共轭加成反应为全碳季碳立体中心的对映选择性构建提供了一种新的有用方法。
