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伯胺/(+)-CSA 盐促进的硝基酯与烯酮的有机催化共轭加成。

Primary amine/(+)-CSA salt-promoted organocatalytic conjugate addition of nitro esters to enones.

机构信息

Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Republic of Singapore, 117543.

出版信息

Org Lett. 2010 May 21;12(10):2278-81. doi: 10.1021/ol1006407.

Abstract

The combination of 9-amino-9-deoxy-epi-cinchonine and (+)-CSA resulted in a novel primary amine-based organocatalyst for effective iminium activation of alpha,beta-unsaturated ketones. Such a catalytic system could catalyze the conjugate addition of nitroacetate to enones in a highly enantioselective manner, affording the desired adducts in high yields and with up to 99% ee.

摘要

9-氨基-9-去氧表小檗碱与(+)-CSA 的组合产生了一种新型的基于伯胺的有机催化剂,可有效活化α,β-不饱和酮的亚胺。这种催化体系可以以高度对映选择性的方式催化硝基乙酸酯与烯酮的共轭加成,以高收率和高达 99%的对映选择性得到所需的加合物。

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