可调节的烯胺酮和α-重氮化合物的[3 + 2]和[2 + 1]环加成反应用于异构异恶唑的合成：金属控制的选择性。

Tunable Key [3 + 2] and [2 + 1] Cycloaddition of Enaminones and α-Diazo Compounds for the Synthesis of Isomeric Isoxazoles: Metal-Controlled Selectivity.

机构信息

National Engineering Research Center for Carbohydrate Synthesis, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, People's Republic of China.

出版信息

Org Lett. 2023 Mar 31;25(12):2139-2144. doi: 10.1021/acs.orglett.3c00636. Epub 2023 Mar 22.

DOI:10.1021/acs.orglett.3c00636

PMID:36946543

Abstract

The three-component reactions of enaminones, α-diazo esters/ketones, and -butyl nitrite (TBN) for the switchable synthesis of isomeric isoxazoles have been realized. The catalysis with Cu(II) salt provides 3,4-disubsituted isoxazoles via [3 + 2] cycloaddition. On the other hand, the catalysis of Ag(I) with identical substrates leads to isomeric isoxazoles with reversed C3 and C4 substitution based on a key [2 + 1] cycloaddition.

摘要

烯胺酮、α-重氮酯/酮和 - 丁基硝化物（TBN）的三组分反应已经实现了用于异构异恶唑的可切换合成。铜(II)盐催化通过[3 + 2]环加成得到 3,4-二取代异恶唑。另一方面，相同底物的 Ag(I)催化导致基于关键[2 + 1]环加成的异构异恶唑具有相反的 C3 和 C4 取代。