Asymmetric catalytic aza-Morita-Baylis-Hillman reaction (aza-MBH): an interesting functional group-caused reversal of asymmetric induction

A highly effcient aza-Morita-Baylis-Hillman reaction ( aza-MBH reaction) of N-tosyl salicylaldehyde imines with alpha,beta-unsaturated ketones has been achieved by using beta-isocupreidine ( beta-ICPD) as the catalyst ( 10 mol%) to give the corresponding adducts in good to high yields ( 90%-quant.) and excellent ee's ( up to 99% ee), with adducts showing the opposite absolute configuration to that of those obtained in the similar aza-MBH reaction of N-tosyl aldimines with alpha,beta-unsaturated ketones.