Asymmetric Direct Vinylogous Michael Additions of Allyl Alkyl Ketones to Maleimides through Dienamine Catalysis

A direct catalytic asymmetric γ-regioselective vinylogous Michael addition of allyl alkyl ketones to maleimides has been developed through dienamine catalysis of a simple chiral 1,2-diphenylethanediamine, giving multifunctional products in excellent enantioselectivity and with high yields. The success of this catalytic strategy relies on the unique inducing effect of deconjugated β,γ-C═C bond, which facilitates the formation of the otherwise unfavored extended dienamine species.