Enantioselective Nickel-Catalyzed α-Spirocyclization of Lactones.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-08-16 Epub Date: 2024-08-01 DOI:10.1021/acs.orglett.4c01661

Allison M Stanko, Melissa Ramirez, Adrian J de Almenara, Scott C Virgil, Brian M Stoltz

引用次数: 0

Abstract

Herein we report a strategy for the enantioselective synthesis of spirocycles containing all-carbon quaternary centers via nickel-catalyzed intramolecular addition of lactone enolates to aryl nitriles. The established lactone α-spirocyclization efficiently and enantioselectively forges 5-, 6-, and 7-membered rings, performing best in the synthesis of 7-membered rings (up to 90% ee). This discovery represents an expansion of the synthetic toolkit for enantioselective spirocyclization, providing access to chiral, pharmaceutically relevant spirocyclic products.

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镍催化的内酯对映体选择性α-螺环化。

在此，我们报告了一种通过镍催化内酯烯醇与芳基腈的分子内加成，对映选择性合成含有全碳季中心的螺环的策略。已建立的内酯α-螺环化技术可高效地对映选择性地生成 5、6 和 7 元环，在合成 7 元环方面表现最佳（ee 值高达 90%）。这一发现拓展了对映体选择性螺环化的合成工具包，提供了获得手性医药相关螺环产品的途径。

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.