Iridium-catalyzed highly enantioselective and chemodivergent coupling reaction of vinyl azides and vinyl benzoxazinones†

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-11-15 DOI:10.1039/D4QO01862A

Deli Gan, Sumei Zhao, Min Yang, Minghui Xu, Bin Chen, Hai-Liang Ni, Wenhao Yu, Bi-Qin Wang, Ping Hu and Peng Cao

引用次数: 0

Abstract

The first iridium-catalyzed enantioselective coupling reaction of vinyl azides and vinyl benzoxazinones is presented. Vinyl azides underwent a tandem allylic alkylation/interrupted Schmidt rearrangement process to produce enantioenriched 3,4-dihydroquinolin-2(1H)-imines, a new class of N-heterocycles. In the presence of CH₃CO₂H, a conventional asymmetric allylic substitution occurred to provide access to nonracemic allylic amides. The synthetic transformations of the product were carried out to construct chiral amines, amides and N-hetero polycycles.

Abstract Image

查看原文本刊更多论文

铱催化的乙烯基叠氮化物和乙烯基苯并噁嗪酮的高对映选择性和化学发散性偶联反应

本文首次介绍了铱催化的乙烯基叠氮化物和乙烯基苯并恶嗪酮的对映选择性偶联反应。乙烯基叠氮化物经过串联烯丙基烷基化/间歇施密特重排过程，生成了对映体富集的 3,4-二氢喹啉-2(1H)-亚胺，这是一类新的 N-杂环化合物。在 CH3CO2H 的存在下，发生了传统的不对称烯丙基取代反应，从而获得了非外消旋烯丙基酰胺。通过对产物进行合成转化，构建了手性胺、酰胺和 N-杂环。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.