Phosphine-catalyzed [3 + 2]-annulation of Morita–Baylis–Hillman carbonates with benzofuran-derived azadienes: Synthesis of spiro-cyclopentane benzofurans

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-05-09 DOI:10.1016/j.tet.2025.134703

Wanxing Liu , Yandong Lv , Xiuzheng Liu , Menghui Guo , Rui Yan , Lingang Wu , Lei Xie , Zhaoxue Wang

引用次数: 0

Abstract

Herein, a phosphine-catalyzed [3 + 2] cycloaddition of Morita–Baylis–Hillman carbonates and benzofuran-derived azadienes has been achieved. A wide range of functionalized spiro-cyclopentane benzofurans were obtained in moderate to great yields (36–65 % yields) with moderate to excellent diastereoselectivities (3.6:1->20:1 drs). The protocol is characterized by easy operation, and broad functional group tolerance. Furthermore, the versatility of this methodology was further demonstrated through gram-scale synthesis and a synthetic transformation of the resulting product.

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苯并呋喃衍生氮杂烯催化森田-贝利斯-希尔曼碳酸盐的[3 + 2]环环化：螺环戊烷苯并呋喃的合成

在这里，实现了磷化氢催化的森田-贝利斯-希尔曼碳酸盐和苯并呋喃衍生的氮杂烯的[3 + 2]环加成。广泛的功能化螺环戊烷苯并呋喃以中高收率（36 - 65%收率）获得，具有中高的非对映选择性（3.6:1->20:1 drs）。该方案具有操作简便、功能群容忍度广的特点。此外，这种方法的多功能性通过克级合成和合成产物的转化得到了进一步的证明。

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

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.