Copper-Catalyzed Enantioselective Acylcyanation of Alkenes

An efficient copper-catalyzed asymmetric vicinal dicarbofunctionalization has been developed for the enantioselective acylcyanation of olefins. The protocol avoids the use of expensive photocatalysts, and showcases a broad substrate scope to afford various β-cyano ketones with very high enantiopurity (up to >99:1 er) and yields (up to 86%). A preliminary mechanistic study has also been conducted, which provided valuable insights into the reaction paths. Furthermore, several functional group transformations in β-cyanoketone have been performed to show the wide synthetic utility of the strategy.

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Publication Details

Journal
Organic Letters
Published
2025-07-24
DOI
https://doi.org/10.1021/acs.orglett.5c02373
Citations
2
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.87

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article

Copper-Catalyzed Enantioselective Acylcyanation of Alkenes

Anurag Biswas, Pazhamalai Anbarasan, Subramanian Srikriya
2 citations
Organic Letters
Catalytic C–H Functionalization Methods
1.87
article

Copper-Catalyzed Enantioselective Acylcyanation of Alkenes

Anurag Biswas, Pazhamalai Anbarasan, Subramanian Srikriya
article en
2 citations

Abstract

An efficient copper-catalyzed asymmetric vicinal dicarbofunctionalization has been developed for the enantioselective acylcyanation of olefins. The protocol avoids the use of expensive photocatalysts, and showcases a broad substrate scope to afford various β-cyano ketones with very high enantiopurity (up to >99:1 er) and yields (up to 86%). A preliminary mechanistic study has also been conducted, which provided valuable insights into the reaction paths. Furthermore, several functional group transformations in β-cyanoketone have been performed to show the wide synthetic utility of the strategy.

Organic LettersVol. 27(31)
Indian Institute of Technology Madras (IN)
Science and Engineering Research Board
Openalex Percentile: Top 14%
Catalytic C–H Functionalization Methods
1.87
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