Rhodium-Catalyzed Asymmetric 1,4-Shift/Double-Cyclization Cascade for De Novo Synthesis of Spirolactones

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-02 DOI:10.1021/acs.orglett.6c03980

Jian Chen, Kai Xue, Qing-Xian Xie, Bo Wu, Yong-Gui Zhou

引用次数: 0

Abstract

A rhodium-catalyzed asymmetric 1,4-shift/double-cyclization cascade of alkyne-tethered ketoesters with arylboronic acids was disclosed. This sequence facilitates the de novo synthesis of chiral spirolactones with high enantioselectivities and allows for the formation of three chemical bonds and two rings in a single step. Moreover, synthetic applications of this protocol have been underscored by diverse transformations that afford versatile chiral spirocycles. Mechanistic studies illustrate that this cascade involves a 1,4-rhodium shift.

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铑催化的不对称1,4-移位/双环化级联重新合成螺旋内酯

摘要报道了一种铑催化的炔系酮酯与芳基硼酸的不对称1,4移位/双环化级联反应。该序列有利于高对映选择性的手性旋内酯的重新合成，并允许在一个步骤中形成三个化学键和两个环。此外，该方案的合成应用已通过提供多功能手性螺旋环的多种转化得到强调。机制研究表明，这个级联涉及到1,4-铑位移。

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.