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手性羟基四苯撑催化硼酸对烯酮的不对称共轭加成反应

Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones.

作者信息

Chai Guo-Li, Sun A-Qiang, Zhai Dong, Wang Juan, Deng Wei-Qiao, Wong Henry N C, Chang Junbiao

机构信息

Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, School of Chemistry and Chemical Engineering , Henan Normal University , Xinxiang , Henan 453007 , China.

Institute of Molecular Sciences and Engineering , Shandong University , Qingdao 266237 , China.

出版信息

Org Lett. 2019 Jul 5;21(13):5040-5045. doi: 10.1021/acs.orglett.9b01637. Epub 2019 Jun 19.

Abstract

( S)-2,15-Br-DHTP-catalyzed asymmetric conjugate addition of boronic acids to β-trifluoromethyl α,β-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.

摘要

研究了(S)-2,15-二溴二氢卟吩催化硼酸对β-三氟甲基α,β-不饱和酮和烯酮的不对称共轭加成反应。该反应以中等到高的产率得到相应的迈克尔加成产物,对映选择性优异(对映体比例高达99:1)。该催化体系具有反应条件温和、效率高以及对杂芳基硼酸具有耐受性的特点。

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