Asymmetric Acyclic 1,3-Difunctionalization of Vinyl Carbenes via Site-Selective Vinylogous Mannich-Type Interception of Oxonium Ylides

A novel and highly stereoselective acyclic 1,3-difunctionalization of vinyl metal carbene species has been developed via Rh­(II)/chiral phosphoric acid co-catalyzed three-component reactions of vinyldiazoacetates with alcohols and imines. This innovative approach features excellent regio-, diastereo...

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Bibliographic Details
Published in:Organic letters 2023-07, Vol.25 (29), p.5509-5514
Main Authors: Zheng, Rimei, Xu, Aimin, Zhang, Tianyuan, Li, Pei, Shi, Maoqing, Dong, Shanliang, Hu, Wenhao, Qian, Yu
Format: Article
Language:English
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Summary:A novel and highly stereoselective acyclic 1,3-difunctionalization of vinyl metal carbene species has been developed via Rh­(II)/chiral phosphoric acid co-catalyzed three-component reactions of vinyldiazoacetates with alcohols and imines. This innovative approach features excellent regio-, diastereo-, and enantioselectivities, demonstrating a broad scope and functional group compatibility. Notably, this is the first example of three-component asymmetric acyclic 1,3-difunctionalization with in situ-formed vinyl metal carbenes.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01983