Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Imines

doi:10.6023/cjoc201704017

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (7): 1589-1612.DOI: 10.6023/cjoc201704017 Previous Articles Next Articles

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过渡金属催化的有机硼试剂对亚胺的不对称加成研究进展

陈雕, 徐明华

中国科学院上海药物研究所新药研究国家重点实验室上海 201203

收稿日期:2017-04-12 修回日期:2017-05-02 发布日期:2017-05-10
通讯作者: 徐明华 E-mail:xumh@simm.ac.cn
基金资助:
国家自然科学基金（Nos.21325209，21472205）、上海市优秀学术带头人计划（No.14XD1404400）资助项目.

Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Imines

Chen Diao, Xu Ming-Hua

State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203

Received:2017-04-12 Revised:2017-05-02 Published:2017-05-10
Contact: 10.6023/cjoc201704017 E-mail:xumh@simm.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.21325209,21472205) and the Program of Shanghai Academic Research Leaders (No.14XD1404400).

Chiral amines are important building blocks in organic synthesis, they also present in numerous natural products, biologically active compounds and pharmaceutical agents. In recent years, the use of various organoboron reagents in transition metal-catalyzed reactions has attracted considerable attentions because of their ready avilibility, low toxicity, good air and moisture stability as well as high functional group compatibility. This review summarizes the remarkable progress and advances in transition metal-catalyzed asymmetric addition of organoboron reagents to imines over the past few years, providing an overview of the recent achievements in stereoselective synthesis of α-chiral amines by using chiral auxiliary or chiral catalysis strategies. At the present time, rhodium-based asymmetric catalysis has proven to be the most efficient and reliable approach to furnish highly optically active α-chiral amines. Varieties of chiral ligands including monophosphines, biphosphines, amidomonophosphanes, phosphoramidites, phosphites, dienes, sulfur-olefins, phosphorus-olefins have showed the great potential in many asymmetric additions of organoboron reagents to imines, enabling the access of both secondary and tertiary α-chiral amines with good to excellent enantioselectivities. On the other hand, important progress has been made in developing effective palladium catalysts mainly based on chiral pyridine-oxazoline and phosphine-oxazoline ligands. However, future studies in this area towards the objective of developing more efficient, practical and general methods remain challenging.

Key words: asymmetric synthesis, chiral amine, metal catalysis, asymmetric addition, organoboron

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Chen Diao, Xu Ming-Hua. Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Imines[J]. Chin. J. Org. Chem., 2017, 37(7): 1589-1612.

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过渡金属催化的有机硼试剂对亚胺的不对称加成研究进展

Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Imines

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