Citation: Chen Diao, Xu Ming-Hua. Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Imines[J]. Chinese Journal of Organic Chemistry, ;2017, 37(7): 1589-1612. doi: 10.6023/cjoc201704017 shu

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

Corresponding author: Xu Ming-Hua, xumh@simm.ac.cn
Received Date: 12 April 2017
Revised Date: 2 May 2017
Available Online: 10 July 2017
Fund Project: the National Natural Science Foundation of China 21472205the National Natural Science Foundation of China 21325209the Program of Shanghai Academic Research Leaders 14XD1404400Project supported by the National Natural Science Foundation of China (Nos. 21325209, 21472205) and the Program of Shanghai Academic Research Leaders (No. 14XD1404400)

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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.
- asymmetric synthesis,
- chiral amine,
- metal catalysis,
- asymmetric addition,
- organoboron
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