Asymmetric Sequential α-Amination-Horner-Wadsworth-Emmons Olefination

Significance

An organocatalytic asymmetric one-pot procedure for the construction of γ-­amino-α,β-unsaturated esters has been developed. α-Amination of aldehydes 1 using dibenzyl azodicarboxylate (DBAD) in the presence of 10 mol% of l-proline was followed by subsequent Horner-Wadsworth-Emmons olefination to provide products of type 2 in high overall yields and enantioselectivities. γ-Amino-α,β-unsaturated esters 2 can be transformed into chiral 2-pyrrolidones 3 and 4 under hydrogenation conditions.