分子内Wittig反应合成螺旋环戊二烯吲哚和2-酰基环戊[b]吲哚

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-03 DOI:10.1021/acs.orglett.5c03242

Yu-Hsuan Chen,Ru-Yin Yu,Wey-Chyng Jeng,Chen-Ling Chang,Jhih-Syuan Wu,Digambar Abasaheb Nevrekar,Raghunath Maruti Walunj,Yi-Ru Chen,Gangababu Marri,Wenwei Lin

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引用次数: 0

摘要

本文报道了一种以多样性为导向合成螺旋环戊二烯吲哚和2-酰基环戊[b]吲哚的有效方法。磷酸-1,6- PBu3与α，β,γ，δ-不饱和氧吲哚的加成为磷两性离子提供了关键的中间体和分支点，用于合成这些不同的环产物。值得注意的是，螺旋化合物是通过独特的δ- c -酰化/Wittig反应序列形成的，而质子转移/Wittig/β-酰化反应产生2-酰基环戊[b]吲哚。值得注意的是，本研究首次报道了具有内环双键的α，β-不饱和酯的直接β-酰化反应。

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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Diversity-Oriented Synthesis of Spirocyclopentadiene Oxindoles and 2-Acyl Cyclopenta[b]indoles via Intramolecular Wittig Reaction.

Herein, we report an efficient strategy for the diversity-oriented synthesis of spirocyclopentadiene oxindoles and 2-acyl cyclopenta[b]indoles. A phospha-1,6-addition of PBu3 to α,β,γ,δ-unsaturated oxindoles provides phosphorus zwitterions as key intermediates and a branching point for the synthesis of these diverse cyclic products. Notably, spiro compounds are formed via a unique δ-C-acylation/Wittig reaction sequence, while the proton transfer/Wittig/β-acylation reactions afforded 2-acyl cyclopenta[b]indoles. Significantly, this study discloses the first report of a direct β-acylation reaction of an α,β-unsaturated ester bearing an endocyclic double bond.

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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.