Acyl Transfer-Driven Rauhut-Currier Dimerization of Morita-Baylis-Hillman Ketones.

J Org Chem

Department of Chemistry, School of Chemical Sciences and Pharmacy, Central University of Rajasthan, NH-8, Bandarsindri, Ajmer 305817, Rajasthan, India.

Published: February 2023

A serendipitous Rauhut-Currier dimerization of 1,1-disubstituted activated olefins derived from Morita-Baylis-Hillman adducts was observed in the presence of DABCO. The reaction is driven by the migration of an acyl group and produces multifunctionalized enol esters in yields greater than 90% in most cases, without necessitating column chromatographic purification. The acyl transfer is thought to proceed via a transition state typical of a Morita-Baylis-Hillman (MBH) reaction, supported by a brief mechanistic study involving computational calculations.

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http://dx.doi.org/10.1021/acs.joc.2c02244DOI Listing

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