Photocatalytic Azetidine Synthesis by Aerobic Dehydrogenative [2 + 2] Cycloadditions of Amines with Alkenes
作者:Rajesh Dasi、Alexander Villinger、Malte Brasholz
DOI:10.1021/acs.orglett.2c03291
日期:2022.11.4
dehydrogenative [2 + 2] cycloadditions between amines and alkenes were developed that allow for the stereoselective and high-yielding synthesis of functionalized azetidines. The oxidative formal Aza Paternò–Büchi reactions are induced by photoredox-catalyzed aerobic oxidation of dihydroquinoxalinones 1 as the amines, and in the presence of structurally diverse alkenes 3 intermolecular [2 + 2] cyclization
开发了胺和烯烃之间的光催化脱氢 [2 + 2] 环加成反应,可实现功能化氮杂环丁烷的立体选择性和高产率合成。氧化形式的 Aza Paternò–Büchi 反应是由光氧化还原催化的二氢喹喔啉酮1作为胺类的有氧氧化引起的,并且在结构多样的烯烃3分子间 [2 + 2] 环化为二氢-1 H -azeto [1,2 - ] quinoxalin-3(4 H )-ones 4发生。该方法的效用通过氨基酸衍生的二氢喹喔啉酮1的选择性转化来说明,包括易氧化的赖氨酸和色氨酸衍生物。