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

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.