Vargas-Sanchez Monica, Couty François, Evano Gwilherm, Prim Damien, Marrot Jérome
Laboratoire SIRCOB, UMR CNRS 8086, Université de Versailles Saint Quentin en Yvelines, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France.
Org Lett. 2005 Dec 22;7(26):5861-4. doi: 10.1021/ol052388e.
[reaction: see text] A new entry to enantiopure 3-aminopyrrolidines was developed using a boron trifluoride-mediated rearrangement of 2-aminomethylazetidines. The method is quite general and produces rearranged products in good yield regardless of both substitution pattern and relative stereochemistry of the starting material. A concise stereocontrolled synthesis of (-)-absouline was achieved on the basis of this new method.
[反应：见正文] 通过三氟化硼介导的2-氨甲基氮杂环丁烷重排反应，开发了一种制备对映体纯3-氨基吡咯烷的新方法。该方法适用性广泛，无论起始原料的取代模式和相对立体化学如何，均能以良好的产率得到重排产物。基于此新方法，实现了（-）-阿苏林的简洁立体控制合成。
