Sc(OTf)3催化螺-环氧氧吲哚与γ-去共轭丁烯内酯间的意外[3 + 2]环加成反应

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-03-18 DOI:10.1021/acs.joc.4c02324

Jing-Liang Yu, Qian-Mao Zhang, Guo Cheng, Chun-Chun Tang, Zhen-Yu Yang, Wen-Sheng Li, Li-Xin Wang

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引用次数: 0

摘要

在Sc(OTf)3催化下，发现了γ-解共轭丁烯内酯和螺-环氧氧吲哚之间独特的β位置[3 + 2]环加成反应。在温和的条件下，在一次操作中成功地构建了多种意想不到的螺-氧吲哚与双环γ-内酯和三个连续立体中心融合的[3 + 2]-环加成加合物，产率高达88%，非对映选择性优异（>20:1），这是传统策略难以实现的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

An Unexpected [3 + 2]-Cycloaddition between Spiro-Epoxyoxindoles and γ-Deconjugated Butenolides Catalyzed by Sc(OTf)3

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An Unexpected [3 + 2]-Cycloaddition between Spiro-Epoxyoxindoles and γ-Deconjugated Butenolides Catalyzed by Sc(OTf)3

A unique β-position [3 + 2]-cycloaddition between γ-deconjugated butenolides and spiro-epoxyoxindoles catalyzed by Sc(OTf)₃ has been disclosed. A variety of unexpected [3 + 2]-cycloaddition adducts of spiro-oxindoles fused with bicyclic γ-lactones and three consecutive stereocenters have been successfully constructed in good yields (up to 88%) with excellent diastereoselectivities (>20:1) in one single operation under mild conditions, which is difficult to achieve by traditional strategies.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.