Asymmetric catalytic aza-Morita-Baylis-Hillman reaction (aza-MBH): an interesting functional group-caused reversal of asymmetric induction.
A highly efficient 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-) 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.
Shi
Min
M
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China. Mshi@mail.sioc.ac.cn
Qi
Ming-Juan
MJ
Liu
Xu-Guang
XG