title: Diastereoselective synthesis of delta-aminoacids through domino Ireland-Claisen rearrangement and Michael addition.
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.
authors.affiliation: Departamento de Química Orgánica, Universidad de Salamanca, Salamanca, Spain. nmg@usal.es
authors.forename: Narciso M
authors.initials: NM
authors.lastname: Garrido
authors.forename: Mercedes
authors.initials: M
authors.lastname: García
authors.forename: David
authors.initials: D
authors.lastname: Díez
authors.forename: M Rosa
authors.initials: MR
authors.lastname: Sánchez
authors.forename: F
authors.initials: F
authors.lastname: Sanz
authors.forename: Julio G
authors.initials: JG
authors.lastname: Urones
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids