Palladium-Catalyzed Enantioselective [3 + 2] Cycloaddition of Vinylarylcyclopropanes (VACPs) with Photogenerated Ketenes to Tetrahydrofurans

A palladium-catalyzed asymmetric [3 + 2] cycloaddition of vinylarylcyclopropanes (VACPs) with photogenerated ketenes is disclosed. This method efficiently constructs tetrahydrofurans featuring a quaternary stereocenter with high yields and excellent enantioselectivity (up to 99% ee). The reaction leverages a visible-light-induced Wolff rearrangement of α-diazoketones and employs a tailored chiral P,S-ligand. The aryl substituent on the VACP is proven crucial for achieving high stereocontrol. The protocol demonstrates broad substrate scope and synthetic utility, providing direct access to valuable tetrahydrofurans.

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Publication Details

Journal
Organic Letters
Published
2026-02-10
DOI
https://doi.org/10.1021/acs.orglett.6c00132
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
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article

Palladium-Catalyzed Enantioselective [3 + 2] Cycloaddition of Vinylarylcyclopropanes (VACPs) with Photogenerated Ketenes to Tetrahydrofurans

Yang‐Zi Liu, Zhijie Ling, Wei-Ping Deng, Jianlu Wang
Organic Letters
Cyclopropane Reaction Mechanisms
article

Palladium-Catalyzed Enantioselective [3 + 2] Cycloaddition of Vinylarylcyclopropanes (VACPs) with Photogenerated Ketenes to Tetrahydrofurans

Yang‐Zi Liu, Zhijie Ling, Wei-Ping Deng, Jianlu Wang
article en

Abstract

A palladium-catalyzed asymmetric [3 + 2] cycloaddition of vinylarylcyclopropanes (VACPs) with photogenerated ketenes is disclosed. This method efficiently constructs tetrahydrofurans featuring a quaternary stereocenter with high yields and excellent enantioselectivity (up to 99% ee). The reaction leverages a visible-light-induced Wolff rearrangement of α-diazoketones and employs a tailored chiral P,S-ligand. The aryl substituent on the VACP is proven crucial for achieving high stereocontrol. The protocol demonstrates broad substrate scope and synthetic utility, providing direct access to valuable tetrahydrofurans.

Organic LettersVol. 28(7)
Zhejiang Normal University (CN)
Openalex Percentile: Top 59%
Cyclopropane Reaction Mechanisms
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