A highly stereoselective one-pot reaction of aliphatic aldehydes and cyanoacrylamides has been developed. The one-pot reaction includes an organocatalytic Michael addition followed by an intramolecular hemiaminalization. After reduction, optically enriched 2-piperidinones with three contiguous chiral centers were obtained in up to 95% yield and 9:1 dr with 99% ee.

1,3-Dipolar cycloaddition of conjugated unsaturated ketimine ylides was disclosed. The reaction of glycine ester with a series of β,γ-unsaturated keto esters in the presence of catalytic amount of TFA was found to give structurally diverse and functionally enriched pyrrolidine derivatives 3 in up to 88% yield. These processes feature a hydrolysis of glycine ketimine. A preliminary enantioselective version of the transformation was also investigated.

A new tandem cycloaddition between proline and β,γ-unsaturated α-keto esters was disclosed. Highly functional and diastereomerically pure pyrrolizidine derivatives were obtained in moderate to high yields.