A Tandem Regiospecific [3 + 2] Annulation/Ring Cleavage Reaction for the Synthesis of β-Ketoenamides.

J Org Chem

School of Chemistry and Environmental Engineering, Yancheng Teachers University, Yancheng City 224007, People's Republic of China.

Published: February 2024


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Article Abstract

A series of β-ketoenamines was synthesized from various phenacyl sulfoxides bearing 1-methyl-1-tetrazole and oximes in moderate to excellent yields. The proposed mechanism involved the generation of α-sulfines from sulfoxides through thermolytic elimination, regiospecific formal [3 + 2] annulations, and elimination of SO. This protocol provides convenient access to a variety of synthetically valuable -unprotected β-enaminones with absolute selectivity.

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http://dx.doi.org/10.1021/acs.joc.3c02717DOI Listing

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