Garrido Narciso M, García Mercedes, Díez David, Sánchez M Rosa, Sanz F, Urones Julio G
Departamento de Química Orgánica, Universidad de Salamanca, Salamanca, Spain.
Org Lett. 2008 May 1;10(9):1687-90. doi: 10.1021/ol8001464. Epub 2008 Apr 10.
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.
描述了一种新型多米诺反应——立体选择性的爱尔兰-克莱森重排和不对称迈克尔加成。从拜利斯-希尔曼加合物3a-f出发，使用手性锂酰胺的方法可得到具有高非对映选择性和对映选择性的光学活性γ-取代δ-氨基酸4a-f。该酸可轻松从大规模反应中分离出来，并转化为2,3-二取代哌啶11或2-取代哌啶酸衍生物12。
