Enantioselective Synthesis: Steric and electronic effects of the substrates upon stereoselectivity in the gold(I)-catalyzed aldol reaction with chiral ferrocenylamine ligands,preliminary communication

Enantioselectivity in the gold(I)-catalyzed aldol reaction with chiral ferrocenylamine ligands is strongly dependent upon both the steric and electronic effects of the substrates. In the reaction of pyridine-2-, 3-, and 4-carbaldehydes with ethyl 2-isocyanoacetate, surprisingly and significantly different enantioselectivities were observed in the formation of the cis- and trans-dihydro-oxazoles that must be due to electronic rather than steric effects. The first example of double stereodifferentiation in the gold(l)-catalyzed aldol reaction is reported.