Wipf Peter, Stephenson Corey R J
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. wipf+@pitt.edu
Org Lett. 2003 Jul 10;5(14):2449-52. doi: 10.1021/ol0347141.
[reaction: see text] Hydrozirconation of alkynes followed by in situ transmetalation to dimethylzinc and 1,2-addition to activated ketones and N-diphenylphosphinoylimines leads to tertiary allylic alcohols and amines in high overall yield. With 8-phenylmenthol as the chiral auxiliary, si-face attack proceeds in good to excellent diastereoselectivities.
[反应:见正文] 炔烃经锆氢化反应,然后原位转金属化为二甲基锌,并对活化酮和N-二苯基膦酰亚胺进行1,2-加成,可高收率地得到叔烯丙醇和叔烯丙胺。以8-苯基薄荷醇作为手性助剂时,硅面进攻具有良好至优异的非对映选择性。