Broad Scope Organocatalytic Aza-Michael Addition

Significance

A procedure for asymmetric cinchona alkaloid (1, 2) catalyzed aza-Michael addition of enones 3 and alkoxyamines 4 is reported. The scope of the reaction was demonstrated in several examples with different substituted substrates, affording products in moderate to good yields and good to excellent enantioselectivities. Moreover, the authors provide two possible activation modes. Both involve hydrogen-bonding interactions of the tertiary amine with alkoxyamines 4 and iminium-ion formation between the primary amine and the enones 3.