Nakhla Josephine S, Wolfe John P
Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.
Org Lett. 2007 Aug 16;9(17):3279-82. doi: 10.1021/ol071241f. Epub 2007 Jul 25.
A concise, modular, asymmetric synthesis of cis-2,6-disubstituted piperazines from readily available amino acid precursors is described. The key step in the synthesis is a Pd-catalyzed carboamination of a N1-aryl-N2-allyl-1,2-diamine with an aryl bromide. The products are obtained in 14-20:1 dr, with >97% ee, and the key cyclizations are the first examples of six-membered ring formation via Pd-catalyzed carboamination reactions of unsaturated amines with aryl halides.
本文描述了一种从易得的氨基酸前体出发,简洁、模块化、不对称合成顺式-2,6-二取代哌嗪的方法。该合成的关键步骤是钯催化N1-芳基-N2-烯丙基-1,2-二胺与芳基溴的碳胺化反应。产物的非对映选择性为14:1至20:1,对映体过量值大于97%,关键的环化反应是不饱和胺与芳基卤化物通过钯催化碳胺化反应形成六元环的首例。