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有机催化2-羟基-1,4-萘醌与硝基烯烃的高度对映选择性迈克尔加成反应。

Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes.

作者信息

Zhou Wen-Ming, Liu Han, Du Da-Ming

机构信息

Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, PRC.

出版信息

Org Lett. 2008 Jul 3;10(13):2817-20. doi: 10.1021/ol800945e. Epub 2008 Jun 6.

Abstract

The first organocatalytic enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes for the direct synthesis of chiral nitroalkylated naphthoquinone derivatives was investigated. Good yields and excellent enantioselectivities (up to >99% ee) could be achieved. This organocatalytic asymmetric Michael addition provides an efficient route toward the synthesis of optically active functionalized naphthoquinones.

摘要

研究了首例通过有机催化2-羟基-1,4-萘醌与硝基烯烃的对映选择性迈克尔加成反应直接合成手性硝基烷基化萘醌衍生物。该反应能获得良好的产率和优异的对映选择性(高达>99% ee)。这种有机催化的不对称迈克尔加成为合成光学活性官能化萘醌提供了一条有效途径。

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