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综述与进展

频哪醇硼烷在酮及亚胺的不对称硼氢化中的应用

刘文伯, 陆展   

  1. 浙江大学化学系 杭州 310000
  • 收稿日期:2020-08-21 修回日期:2020-09-08 出版日期:2030-01-01 发布日期:2020-09-16
  • 通讯作者: 陆展 E-mail:luzhan@zju.edu.cn
  • 基金资助:
    国家自然科学基金(No.21922107,21772771)、浙江省自然科学基金(LR19B020001)、中央高校基本科研业务费(2019QNA3008)资助项目.

Application of Pinacolborane in Catalytic Enantioselective Hydroboration of Ketones and Imines

Liu Wenbo, Lu Zhan   

  1. Department of Chemistry, Zhejiang University, Hangzhou 310000
  • Received:2020-08-21 Revised:2020-09-08 Online:2030-01-01 Published:2020-09-16
  • Supported by:
    Project supported by the NSFC (No. 21922107 and 21772171), Zhejiang Provincial Natural Science Foundation of China (LR19B020001), Center of Chemistry for Frontier Technologies, and the Fundamental Research Funds for the Central Universities (2019QNA3008).

手性醇及手性胺化合物广泛应用于有机合成、材料科学、医药、农用化学及精细化工,酮及亚胺的不对称硼氢化反应为制备该类化合物提供了有效手段。频哪醇硼烷,自1991年被报道以来,作为一种稳定的、商品化的、易定量的有机硼试剂被广泛应用于羰基化合物、亚胺及腈类化合物的还原反应及其机理研究中。在过去的5年里,频哪醇硼烷也被应用于不对称硼氢化反应以制备手性醇及手性胺。本综述按不同的催化剂,如地球丰产过渡金属、主族元素及稀土金属分类,介绍频哪醇硼烷参与的酮和亚胺的不对称催化硼氢化反应。

关键词: 频哪醇硼烷, 不对称硼氢化, 廉价金属, 酮, 亚胺

Enantioselective hydroboration of ketones and imines provides a powerful method to access valuable chiral alcohols and amines which are widely used in organic synthesis, materials science, pharmaceutical, agrochemistry, and fine chemical industry. After invented in 1991, pinacolborane (HBpin) as a stable, commercially available and measurably simple reductive reagent has been widely applied in hydroboration of carbonyl derivatives, imines and nitriles and relevant mechanistic investigation. In the past 5 years, HBpin has also been employed for asymmetric catalytic hydroboration (CHB) to access chiral alcohols and amines. This review outlines enantioselective CHB reactions of ketones and imines using HBpin, and is classified based on catalysts such as earth abundant transition metals, main group elements, and rare-earth metals.

Key words: pinacolborane, asymmetric hydroboration, earth abundant transition metal, ketone, imine