Stereoselective Synthesis of Olefins from β-Hydroxy NHPI Esters

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-11 DOI:10.1021/acs.orglett.5c00211

Fengyuan He, Yu Huang, Long Jiang, Wenbo H. Liu

引用次数: 0

Abstract

Herein, we describe a highly stereoselective method to access a single olefin isomer from readily available β-hydroxy N-hydroxyphthalimide (NHPI) esters. Depending on the configuration of the precursor (anti or syn), either the E or Z olefin is prepared selectively under Lewis acid-promoted conditions. Without involving radical chemistry, a β-lactone is proposed as the key intermediate in this decarboxylative olefination.

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β-羟基NHPI酯立体选择性合成烯烃的研究

在这里，我们描述了一种高度立体选择性的方法，从现成的β-羟基n -羟基邻苯二胺（NHPI）酯中获得单一的烯烃异构体。根据前驱体的构型（反或顺），在路易斯酸促进条件下选择性地制备E或Z烯烃。在不涉及自由基化学的情况下，β-内酯被提出作为脱羧烯烃的关键中间体。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.