Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, United States.
J Org Chem. 2013 Jun 21;78(12):6131-42. doi: 10.1021/jo400788a. Epub 2013 Jun 5.
We report a facile approach to a cyclopropyl-fused pyrrolidine, which contains four stereogenic centers, by employing the N-O tethered carbenoid methodology. The synthesis was facilitated by the development of a direct Mitsunobu reaction of alcohols with N-alkyl-N-hydroxyl amides to give diazo precursors, which upon intramolecular cyclopropanation yielded a library of N-O containing cyclopropyl-fused bicyclic intermediates. Elaboration of the N-O moiety of one member of this library resulted in the formation of the desired pyrrolidine ring demonstrating the potential of this methodology for making cyclopropyl-fused heterocycles.
我们报告了一种通过 N-O 键连接的卡宾原子转移方法来合成含有四个手性中心的环丙基并吡咯烷的简便方法。该合成方法的开发得益于醇与 N-烷基-N-羟基酰胺的直接 Mitsunobu 反应，得到重氮前体，然后进行分子内环丙基化反应，得到一系列含有 N-O 的环丙基并双环中间体库。对这个文库中的一个成员的 N-O 部分进行详细研究，导致形成所需的吡咯烷环，证明了这种方法用于合成环丙基并杂环的潜力。
