Nine-Membered Ketolactams by Oxidative Cyclization Expansion

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-27 DOI:10.1021/acs.orglett.5c0146210.1021/acs.orglett.5c01462

Yun Yang, Ben Ebel, Iris M. Oppel and Frederic W. Patureau*,

引用次数: 0

Abstract

Considerable progress has been made over decades in synthetic organic chemistry in order to build up molecular complexity, often through the design of advanced catalytic systems. Yet, simply exposing organic molecules to benchmark oxidants in catalyst free conditions can sometimes lead to surprising and highly valuable products. Thus, a synthetic method for accessing rare 9-membered ketolactams is herein described, under mild oxidative conditions. Key ¹⁸O and ¹⁷O label experiments revealed an unexpected oxygen atom migration event in the ring expansion process. The scope, mechanism, synthetic applications, and 9 to 7 membered ring contraction opportunities are discussed.

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氧化环化扩张的九元酮内酰胺

几十年来，为了构建分子复杂性，通常通过设计先进的催化系统，合成有机化学取得了相当大的进展。然而，简单地将有机分子暴露在无催化剂条件下的基准氧化剂中，有时会产生令人惊讶的高价值产品。因此，本文描述了在温和氧化条件下获取稀有9元酮内酰胺的合成方法。关键的18O和17O标记实验揭示了环膨胀过程中意想不到的氧原子迁移事件。讨论了收缩的范围、机理、合成应用以及9 ~ 7元环收缩的机会。

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.