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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 2: 255 - 275

DOI: https://doi.org/10.6023/cjoc201910009

Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Aldehydes and Ketones

  • Zhu Dong-Xing ,
  • Xu Ming-Hua
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  • a State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203;
    b Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055

Received date: 2019-10-10

  Revised date: 2019-10-27

  Online published: 2019-11-07

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21672229, 81521005, 21971103) and the National Science & Technology Major Project of China (No. 2018ZX09711002-006).

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Abstract

Chiral aryl alcohols are prevalent in a broad range of biologically active compounds, pharmaceutical agents and natural products. They also constitute a broad class of optically active building blocks for the synthesis of important chiral compounds. In recent years, organoboron reagents are widely used in organic synthesis as they possess advantages of ready availability, low toxicity, good air and moisture stability as well as high functional group compatibility. Since the first report of rhodium-catalyzed asymmetric addition of aryl boronic acids to aryl aldehydes in 1998 by Miyaura, the use of organoboron reagents in asymmetric addition to various carbonyl compounds under various transition-metal catalyses has been intensively investigated. Over the past two decades, transition metal-catalyzed asymmetric addition of organoboron reagents to aldehydes and ketones has proved as one of the most direct and powerful methods for accessing versatile optically active alcohols. The development and progress of a wide range of chiral ligands for Rh, Ru, Pd, Ir, Cu, Ni and Co catalysis for asymmetric addition of organoboron reagents to aldehydes and ketones are summarized, and the achievements in enantioselective synthesis of chiral aryl alcohols and their applications in the synthesis of related biocative products are described. Among them, rhodium and ruthenium-catalyzed enantioselective additions have received considerable attention. In the cases of activated carbonyl compounds such as α-aryl ketoesters and α-diaryl diketones, excellent results can be attained in terms of both yield and enantioselectivity. However, it remains a daunting challenge for highly enantioselective addition to simple unactivated aldehydes and ketones owing to the difficulty in overcoming stereo differentiation. Future efforts in the community would focus on developing new effective transition-metal catalysts in addressing these issues by promoting efficient transformation and controlling excellent enantioselectivity.

Key words： asymmetric synthesis; chiral alcohols; organoboron reagents; transition-metal catalysis; asymmetric addition

Cite this article

Zhu Dong-Xing , Xu Ming-Hua . Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Aldehydes and Ketones[J]. Chinese Journal of Organic Chemistry, 2020 , 40(2) : 255 -275 . DOI: 10.6023/cjoc201910009

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