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.
Authors
- Yang‐Zi Liu (ORCID: https://orcid.org/0000-0001-6702-4507)
- Zhijie Ling
- Wei-Ping Deng
- Jianlu Wang
Institutions
- Zhejiang Normal University (CN)
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
- 0.00