Institut de Chimie Moléculaire de Reims, CNRS (UMR 6229) and Université de Reims, 51687 Reims Cedex 2, France.
Org Lett. 2010 Nov 19;12(22):5128-31. doi: 10.1021/ol102038x. Epub 2010 Oct 18.
A highly diastereoselective synthesis of trans-2-substituted cyclopentylamines via a tandem hydrozirconation/Lewis acid-mediated cyclization sequence applied to butenyl oxazolidines is described. The method allows an easy preparation of diversely substituted cyclopentylamines which appear to be useful synthetic intermediates. This was further illustrated by the syntheses of (±)-Rodocaine, (±)-trans-pentacin, and enantiomerically enriched trans-cyclopentane-1,2-diamine.
通过串联的氢化锆/路易斯酸介导的环化序列，高非对映选择性地合成了反式-2-取代的环戊基胺，该方法适用于丁烯基恶唑烷。该方法可以很容易地制备各种取代的环戊基胺，这些胺似乎是有用的合成中间体。（±）-Rodocaine、（±）-反式戊辛因和对映体富集的反式-1,2-环戊烷二胺的合成都进一步说明了这一点。
