Asymmetric Transfer Hydrogenations of β-Enamine Cyanide with Chiral Ammonia Borane

doi:10.6023/cjoc201904079

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2188-2195.DOI: 10.6023/cjoc201904079 Previous Articles Next Articles

Special Issue: 陈茹玉先生诞辰100周年

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基于手性氨硼烷的β-烯胺腈不对称转移氢化反应

周启文^a, 冯向青^b, 杨晶^a, 杜海峰^b

a 北京化工大学生命科学与技术学院化工资源有效利用国家重点实验室北京 100029;
b 中国科学院化学研究所北京国家分子科学研究中心中国科学院分子识别与功能重点实验室北京 100190

收稿日期:2019-04-30 修回日期:2019-06-06 发布日期:2019-06-12
通讯作者: 杨晶, 杜海峰 E-mail:yangji@mail.buct.edu.cn;haifengdu@iccas.ac.cn
基金资助:
国家自然科学基金（Nos.21825108，91856103）资助项目.

Asymmetric Transfer Hydrogenations of β-Enamine Cyanide with Chiral Ammonia Borane

Zhou Qiwen^a, Feng Xiangqing^b, Yang Jing^a, Du Haifeng^b

a Key Laboratory of Chemical Resource Engineering Beijing Key Laboratory of Bioprocess, College of Life Sciences and Technology, Beijing University of Chemical Technology, Beijing 100029;
b Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190

Received:2019-04-30 Revised:2019-06-06 Published:2019-06-12
Contact: 10.6023/cjoc201904079 E-mail:yangji@mail.buct.edu.cn;haifengdu@iccas.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21825108, 91856103).

1. Asymmetric Transfer Hydrogenations of β-Enamine Cyanide with Chiral Ammonia Borane.PDF(9598KB)

Abstract

The asymmetric transfer hydrogenation represents one important class of reactions for the synthesis of optically active compounds. A chiral ammonia borane was generated in situ from an H₂ release reaction between chiral phosphoric acid and ammonia borane, which could be regenerated by the assistance of water after the hydrogen transfer process and made this reaction catalytic. With this chiral ammonia borane, asymmetric transfer hydrogenations of β-enamine cyanides were realized to afford the desired products in 48%~98% yields with 61%~95% ee.

Key words: asymmetric transfer hydrogenation, chiral ammonia borane, chiral phosphoric acid, ammonia borane, β-enamino cyanide

Cite this article

Zhou Qiwen, Feng Xiangqing, Yang Jing, Du Haifeng. Asymmetric Transfer Hydrogenations of β-Enamine Cyanide with Chiral Ammonia Borane[J]. Chin. J. Org. Chem., 2019, 39(8): 2188-2195.

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基于手性氨硼烷的β-烯胺腈不对称转移氢化反应

Asymmetric Transfer Hydrogenations of β-Enamine Cyanide with Chiral Ammonia Borane

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