Stereoselective Vinylogous Mukaiyama Aldol Reaction of α-Haloenals

We have developed a high-yielding and stereoselective vinylogous Mukaiyama aldol reaction (VMAR) of alpha-haloenals. Contrary to the simple alpha,beta-unsaturated aldehyde, alpha-haloenals were found to be reactive affording the corresponding VMAR adducts in excellent yields. Some transformations of VMAR adducts by Pd-mediated cross-coupling were also examined in order to demonstrate the synthetic utility of VMAR of alpha-haloenals.