Asymmetric Electrophilic Amination of Various Carbon Nucleophiles with Enantiomerically Pure Chiral <i>N</i>-H Oxaziridines Derived from Camphor and Fenchone
作者:Philip C. Bulman Page、Corinne Limousin、Victor L. Murrell
DOI:10.1021/jo020306j
日期:2002.11.1
The first two stable enantiomerically pure chiral N-H oxaziridines, derived from camphor and fenchone, are shown to act as electrophilic sources of nitrogen upon reaction with various carbon nucleophiles. Nitrogen is transferred, together with the camphor/fenchone unit, when deprotonated esters, malonates, and nitriles are used as nucleophiles. One of the ester or nitrile units in the substrate usually
衍生自樟脑和fenchone的前两个稳定的对映体纯净的手性NH恶唑烷经显示与各种碳亲核试剂反应后可作为氮的亲电子源。当使用去质子化的酯,丙二酸酯和腈作为亲核试剂时,氮会与樟脑/芬琴酮单元一起转移。底物中的酯或腈单元之一通常会水解;提出了一种循环机制来解释这一现象。