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2022 , Vol. 42 >Issue 10: 3118 - 3128

DOI: https://doi.org/10.6023/cjoc202208043

综述与进展

钯催化的磷、硫和硅中心手性化合物的合成进展

  • 张洁明 ,
  • 倪航 ,
  • 吴起 ,
  • 杨俊锋 ,
  • 张俊良
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  • a 浙江大学化学系 杭州 310027
    b 浙江省化工研究院有限公司 杭州 310023
    c 复旦大学化学系 上海 200438

收稿日期: 2022-08-31

  修回日期: 2022-10-20

  网络出版日期: 2022-10-25

基金资助

国家重点研发计划(2021YFF0701600); 国家自然科学基金(22031004); 国家自然科学基金(21921003); 国家自然科学基金(91956128); 上海市科学技术委员会(21ZR1445900); 上海市教育委员会(20212308)

收起

Development of P, S and Si-Stereogenic Compounds Synthesis via Palladium Catalysis

  • Jieming Zhang ,
  • Hang Ni ,
  • Qi Wu ,
  • Junfeng Yang ,
  • Junliang Zhang
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  • a Department of Chemistry, Zhejiang University, Hangzhou 310027
    b Zhejiang Research Institute of Chemical Industry, Hangzhou 310023
    c Department of Chemistry, Fudan University, Shanghai 200438
*Corresponding author. E-mail: ;
E-mail:

Received date: 2022-08-31

  Revised date: 2022-10-20

  Online published: 2022-10-25

Supported by

National Key R&D Program of China(2021YFF0701600); National Natural Science Foundation of China(22031004); National Natural Science Foundation of China(21921003); National Natural Science Foundation of China(91956128); Science and Technology Commission of Shanghai Municipality(21ZR1445900); Shanghai Municipal Education Commission(20212308)

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摘要

含有磷、硫和硅三类杂原子中心手性的化合物在医药、农药、材料等领域有着广泛的应用, 高效构建这三类杂原子中心手性已经逐步发展成为不对称合成化学重要的前沿课题之一. 着重介绍了钯在手性配体或者助剂参与下, 高效构建磷、硫和硅中心手性化合物的方法. 在P中心手性构建方面, 主要从膦氢或膦-硅(氧)键活化、P中心去对称化以及环加成等策略进行介绍. 硫和硅中心手性化合物的发展稍晚, 合成策略有些类似. 对一些代表性的反应机理也做了介绍, 同时介绍了一些潜在的应用.

关键词： 钯催化; 磷手性; 硫手性; 硅手性; 不对称催化

本文引用格式

张洁明 , 倪航 , 吴起 , 杨俊锋 , 张俊良 . 钯催化的磷、硫和硅中心手性化合物的合成进展[J]. 有机化学, 2022 , 42(10) : 3118 -3128 . DOI: 10.6023/cjoc202208043

Abstract

Compounds bearing phosphorus, sulfur or silicon stereogenic center have a wide range of applications in the fields of medicine, pesticides, organic synthesis and material science. Efficient construction of these three types of heteroatom-centered chirality has gradually developed as one of the most important frontiers in asymmetric synthetic chemistry. This paper focuses on the recent development of the asymmetric synthesis via palladium/chiral complexes or using the chiral auxiliaries. Strategies such as P—X (X=H, Si or O) bond activation, desymmetrization, and cycloaddition for P-chiral compounds synthesis are introduced, while the methods for S and Si chiral compounds are somewhat similar. The mechanism of some representative examples and their potential applications are also included.

Key words： palladium catalysis; P-chirality; S-chirality; Si-chirality; asymmetric catalysis

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