Cu(II)-NHC Catalyzed Insertion of Quinoid Carbenes into cis-Epoxides: Stereoselective Synthesis of trans-Dihydronaphthodioxine

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-01-28 DOI:10.1021/acs.orglett.5c00020

Satabdi Bera, Subarna Pan, Rajarshi Samanta

引用次数: 0

Abstract

A straightforward synthesis of trans-dihydronaphthodioxine has been efficiently accomplished through Cu(II)-NHC catalysis, involving the stereoselective ring opening of cis-epoxides with quinoid-carbene. Intramolecular S_N2-like substitution facilitates the inversion of stereochemistry during cis-epoxide ring opening. This reaction has been developed under simple conditions, demonstrating a broad substrate scope with a wide chemoselective profile. Additionally, late-stage functionalization of complex bioactive molecules has been successfully achieved.

Abstract Image

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

求助全文

约1分钟内获得全文去求助

来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.