Thiazolylidene-catalyzed cleavage of methyl oleate-derived α-hydroxy ketone to the corresponding free aldehydes

Abstract

The thiazolylidene-catalyzed cleavage of the α-hydroxy ketone derived from methyl oleate gave the corresponding aldehydes under nonoxidative conditions through a retro-benzoin process. The aldehydes produced are in equilibrium with their corresponding acyloins. To illustrate the synthetic utility of this protocol, the aldehydes were recovered by distillation.

Keywords: aldehydes; biomass; carbenes; cleavage reactions; organocatalysis.