Rhodium-Catalyzed Enal Transfer with N‑Methoxypyridazinium Salts

Herein, we report a simple method for functionalized enals involving enal-transfer reaction of water-soluble N-methoxypyridazinium salts. This open-flask reaction proceeds under mild aqueous basic conditions through [2,3]-sigmatropic rearrangement of propargyl/allyl sulfur-ylides derived from in sit...

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Bibliographic Details
Published in:Organic letters 2022-06, Vol.24 (21), p.3850-3854
Main Authors: Kanchupalli, Vinaykumar, Thorbole, Laxman Anandrao, Kalepu, Jagadeesh, Joseph, Desna, Arshad, Mohammad, Katukojvala, Sreenivas
Format: Article
Language:English
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Summary:Herein, we report a simple method for functionalized enals involving enal-transfer reaction of water-soluble N-methoxypyridazinium salts. This open-flask reaction proceeds under mild aqueous basic conditions through [2,3]-sigmatropic rearrangement of propargyl/allyl sulfur-ylides derived from in situ-generated Rh-(E)-enalcarbene. Various synthetically challenging allene- and allyl-functionalized (E)-enals with a γ-C­(sp3) quaternary center were obtained in good to high yields. InCl3-catalyzed cascade cyclization of allenyl-enal and aniline gave a valuable pyrrolo­[1,2-a]­quinoline motif.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01424