Sulfinyl-Imine-Assisted Asymmetric [3,3]-Sigmatropic Rearrangement: Generation of Tertiary and Quaternary Stereocenters.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-02 DOI:10.1021/acs.orglett.5c03577

Ganesh Karan,Susanta Bhunia,Shubham Snehil,Modhu Sudan Maji

引用次数: 0

Abstract

An asymmetric chemoselective allylation followed by an oxy-Cope rearrangement sequence is developed to efficiently synthesize chiral β-allylated ketoimines bearing quaternary stereocenters in excellent yields and diastereoselectivities. Besides acting as a nucleophile, allylboronic acid also plays the vital role of a Lewis acid promoter, eliminating the need for adding any external catalyst. Applicability of this method was demonstrated by the total syntheses of flustramine alkaloids.

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亚胺辅助不对称[3,3]-异位重排：叔、季立体中心的生成。

采用不对称化学选择性烯丙基化后的氧- cope重排序列，以优异的产率和非对映选择性，有效地合成了手性β-烯丙基化的含季立体中心酮亚胺。除了作为亲核试剂，烯丙基硼酸还起着Lewis酸促进剂的重要作用，无需添加任何外部催化剂。以氟曲明生物碱的全合成为例，验证了该方法的适用性。

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.