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

Abstract

A highly efficient aza-Morita–Baylis–Hillman reaction (aza-MBH reaction) of N-tosyl salicylaldehyde imines with α,β-unsaturated ketones has been achieved by using β-isocupreidine (β-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 α,β-unsaturated ketones.