A switch of facial selectivities using alpha-heteroatom-substituted aldehydes in the vinylogous Mukaiyama aldol reaction.Org Lett. 2009 Mar 19; 11(6):1277-80.OL
The vinylogous Mukaiyama aldol reaction (VMAR) of chiral nonracemic ketene silyl N,O-acetal with various aldehydes is demonstrated. VMAR with alpha-heteroatom-unsubstituted aldehydes proceeded with a high degree of anti-selectivity. In sharp contrast, moderate to high syn-selectivity was observed when alpha-heteroatom-substituted aldehydes were used.