Stereoselective Synthesis of Olefins from β-Hydroxy NHPI Esters

IF 4.9 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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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.