Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (3): 961-973.DOI: 10.6023/cjoc202211045 Previous Articles     Next Articles

Special Issue: 中国女科学家专辑

REVIEWS

不对称催化质子化构建α-叔碳羰基化合物研究进展

曹伟地, 刘小华*()   

  1. 四川大学化学学院 成都 610064
  • 收稿日期:2022-11-30 修回日期:2023-02-03 发布日期:2023-02-14
  • 通讯作者: 刘小华
  • 基金资助:
    国家自然科学基金(22071160); 四川省科技计划(2021YJ0562)

Recent Advances on Catalytic Enantioselective Protonation for Construction of α-Tertiary Carbonyl Compounds

Weidi Cao, Xiaohua Liu()   

  1. College of Chemistry, Sichuan University, Chengdu 610064
  • Received:2022-11-30 Revised:2023-02-03 Published:2023-02-14
  • Contact: Xiaohua Liu
  • Supported by:
    National Natural Science Foundation of China(22071160); Sichuan Science and Technology Program(2021YJ0562)

Catalytic enantioselective protonation (EP) is a straightforward and effective approach to construct enantioenriched carbonyl compounds containing a tertiary stereocenter at its α-position, which has been widely applied in organic synthesis and medicinal chemistry. This field has significant advances in recent decades, and relevant reviews based on substrate category, catalytic system and reaction type have been reported successively. In this paper, new developments in this field are updated and summarized since 2019, which are classied into the directly catalytic asymmetric protonation of performed enolates and the enantioselective protonation of in situ enolates, α-carbanion, or α-radical intermediates, involving a variety of substrate categories, catalytic systems, activation modes, as well as catalytic strategies and means. It is expected that these studies can inspire chemists to continuously contribute to this field and further promote the development of carbonyl chemistry, asymmetric catalysis and other related fields, and provide facile and efficient access to high-value chiral molecules, including natural products and their intermediates, drugs, drug candidates and so on.

Key words: asymmetric catalysis, protonation, chiral carbonyl compound, α-tertiary stereocenter, enolate, organocatalysis, Lewis acid catalysis