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Synthesis
DOI: 10.1055/a-2726-4179
Short Review

Recent Advances in Cr-Catalyzed Asymmetric Nozaki–Hiyama–Kishi Reaction: From Alkyl Electrophiles to Alkyl Nucleophiles

Authors

  • Haigen Shen

    1   Department of Chemistry, Westlake University, Hangzhou, China (Ringgold ID: RIN557712)

  • Feng-Hua Zhang

    2   School of Pharmaceutical Science and Technology, UCAS Hangzhou Institute for Advanced Study, Hangzhou, China (Ringgold ID: RIN638898)

  • Zhaobin Wang

    1   Department of Chemistry, Westlake University, Hangzhou, China (Ringgold ID: RIN557712)
    3   Institute of Natural Sciences, Westlake Institute for Advanced Study, Hangzhou, China (Ringgold ID: RIN523194)

Supported by: Zhejiang Provincial Key Laboratory Construction Project 2025ZY01063
Supported by: National Natural Science Foundation of China 22171231
Supported by: Zhejiang Provincial Natural Science Foundation of China LR25B020004,XHD23B0101
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The Nozaki-Hiyama-Kishi (NHK) reaction is renowned for its excellent chemoselectivity and functional group compatibility in carbonyl additions, and has been widely applied in natural product synthesis. However, its development remained relatively dormant for a long time, largely due to limitations such as the limited diversity of radical precursors, the narrow structural diversity of products, and the need for stoichiometric metal reductants and dissociation reagents.Recently, the reaction has witnessed significant progress, driven by advances in asymmetric radical chemistry as well as photo-and electrochemistry. In this review, we summarize key developments in chromium-catalyzed asymmetric NHK reactions over the past decade, covering substrate scope, stereocontrol, and mechanistic insights, and discuss the opportunities and challenges that remain in this field.



Publication History

Received: 22 August 2025

Accepted after revision: 17 October 2025

Accepted Manuscript online:
17 October 2025

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