Substrate-Directed Enantioselective Aziridination of Alkenyl Alcohols Controlled by a Chiral Cation
作者:Alexander Fanourakis、Nicholas J. Hodson、Arthur R. Lit、Robert J. Phipps
DOI:10.1021/jacs.3c00693
日期:——
Alkene aziridination is a highly versatile transformation for the construction of chiral nitrogen-containing compounds. Inspired by the success of analogous substrate-directed epoxidations, we report an enantioselective aziridination of alkenyl alcohols, which enables asymmetric nitrene transfer to alkenes with varied substitution patterns, including those not covered by the current protocols. We believe
烯烃氮丙啶化是一种用于构建手性含氮化合物的高度通用的转化。受类似的底物导向环氧化反应成功的启发,我们报告了烯基醇的对映选择性氮丙啶化,它使不对称的氮烯转移到具有不同取代模式的烯烃,包括那些当前协议未涵盖的烯烃。我们相信我们的方法是有效的,因为它是底物导向的,利用了底物、非手性双离子铑 (II,II) 四羧酸二聚体及其两个相关的金鸡纳生物碱衍生阳离子之间有吸引力的非共价相互作用网络。正是这些阳离子提供了确定的手性口袋,氮丙啶化可以在其中发生。除了对兼容的烯烃类进行全面评估外,