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通过有机催化溴丙二酸酯对α,β-不饱和硝基烯烃的共轭加成实现硝基环丙烷的高对映选择性合成。

Highly enantioselective synthesis of nitrocyclopropanes via organocatalytic conjugate addition of bromomalonate to alpha,beta-unsaturated nitroalkenes.

作者信息

Xuan Yi-Ning, Nie Shao-Zhen, Dong Li-Ting, Zhang Jun-Min, Yan Ming

机构信息

Industrial Institute of Fine Chemicals and Synthetic Drugs, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.

出版信息

Org Lett. 2009 Apr 2;11(7):1583-6. doi: 10.1021/ol900227j.

DOI:10.1021/ol900227j
PMID:19260703
Abstract

Highly enantioselective synthesis of nitrocyclopropanes was achieved via the organocatalytic conjugate addition of dimethyl bromomalonate to nitroalkenes and the consequent intramolecular cyclopropanation. 6'-Demethyl quinine was found to be the efficient catalyst. Excellent enantioselectivities, diastereoselectivities, and good yields were obtained for a variety of aryl or heteroaryl nitroethylenes.

摘要

通过丙二酸二甲酯对硝基烯烃的有机催化共轭加成以及随后的分子内环丙烷化反应，实现了硝基环丙烷的高度对映选择性合成。发现6'-去甲基奎宁是有效的催化剂。对于多种芳基或杂芳基硝基乙烯，获得了优异的对映选择性、非对映选择性和良好的产率。

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