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Synthesis
DOI: 10.1055/a-2726-4179
DOI: 10.1055/a-2726-4179
Short Review
Recent Advances in Cr-Catalyzed Asymmetric Nozaki–Hiyama–Kishi Reaction: From Alkyl Electrophiles to Alkyl Nucleophiles
Autoren
We are grateful for financial support from the Zhejiang Provincial Natural Science Foundation of China (XHD23B0101, LR25B020004), National Natural Science Foundation of China (22171231), and Zhejiang Provincial Key Laboratory Construction Project (2025ZY01063).
Gefördert durch: National Natural Science Foundation of China 22171231
Gefördert durch: Zhejiang Provincial Natural Science Foundation of China LR25B020004,XHD23B0101
Abstract
The Nozaki–Hiyama–Kishi (NHK) reaction is renowned for its excellent chemoselectivity and functional-group compatibility in carbonyl additions, and it has been widely applied in natural product synthesis. However, its development has remained relatively dormant for a long time, largely due to restricted diversity of radical precursors, the narrow structural diversity of products, and the need for stoichiometric metal reductants and dissociating reagents. Recently, the reaction has witnessed significant progress, driven by advances in asymmetric radical chemistry, as well as photochemistry 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.
Keywords
Cr-catalyzed - NHK reaction - Reductive coupling - Photoredox-neutral coupling - Alkyl electrophiles - Alkyl nucleophilesPublikationsverlauf
Eingereicht: 22. August 2025
Angenommen nach Revision: 17. Oktober 2025
Accepted Manuscript online:
17. Oktober 2025
Artikel online veröffentlicht:
14. November 2025
© 2025. Thieme. All rights reserved.
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