Diastereoselective Synthesis Of Delta-Aminoacids Through Domino Ireland-Claisen Rearrangement And Michael Addition

domino reaction-stereoselective Ireland-Claisen rearrangement and asymmetric Michael addition-is described. A protocol starting from Baylis-Hillman adducts 3a-f using chiral lithium amide affords optically active gamma-substituted delta-aminoacids 4a-f with high diastereoselectivities and enantioselectivities. The acid can be isolated easily from large-scale reactions and transformed to 2,3-disubstituted piperidines 11 or 2-substituted nipecotic acid derivates 12.