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