Diastereoselective synthesis of delta-aminoacids through domino Ireland-Claisen rearrangement and Michael addition |
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| Authors: | Garrido Narciso M García Mercedes Díez David Sánchez M Rosa Sanz F Urones Julio G |
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| Affiliation: | Departamento de Química Orgánica, Universidad de Salamanca, Salamanca, Spain. nmg@usal.es |
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| Abstract: | 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 gamma-substituted delta-amino acids 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. |
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