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Diastereoselective Synthesis of δ-Aminoacids through Domino Ireland−Claisen Rearrangement and Michael Addition

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posted on 01.05.2008, 00:00 by Narciso M. Garrido, Mercedes García, David Díez, M. Rosa Sánchez, F. Sanz, Julio G. Urones
A novel 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 γ-substituted δ-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.