Dearomative, Intramolecular Bromoetherification of Carbohydrate-derived Glycosyl Furans: Access to Enantiopure 6-Bromo-Furo[3,2-b]furans

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-04-23 DOI:10.1002/adsc.202500228

William J. Berkey, Lindsey R. C. Bryson, Russell Kirkland, Kaitlyn S. Otte, Christopher Jones, Stefan France

引用次数: 0

Abstract

Glycosyl furans represent versatile chiral platform molecules that can be readily accessed via the Garcia Gonzalez reaction. Herein, we report a dearomative, intramolecular bromoetherification of carbohydrate-derived glycosyl furans to generate enantiopure 6-bromo-furo[3,2-b]furans in up to 69% yield. The method employs N-Br aromatic amides as competent electrophilic halogenating agents that outpace other known reagents. The method works for glycosyl furans derived from the Garcia Gonzalez reactions of various active methylene compounds and unprotected sugars. Further functionalization of the C-Br bond of the 6-bromo-furo[3,2-b]furans is explored as well.

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碳水化合物衍生糖基呋喃的分子内脱芳溴醚化反应：获得对映纯6-溴-呋喃[3,2-b]

糖基呋喃是一种多功能手性平台分子，可以通过加西亚-冈萨雷斯反应轻松获得。在此，我们报告了一种对碳水化合物衍生的糖基呋喃进行脱芳、分子内溴醚化反应生成对映体纯度高达 69% 的 6-溴-呋喃并[3,2-b]呋喃的方法。该方法利用 N-Br 芳香族酰胺作为亲电卤化剂，其效果优于其他已知试剂。该方法适用于由各种活性亚甲基化合物和无保护糖的加西亚-冈萨雷斯反应生成的糖基呋喃。此外，还探索了 6-溴-呋喃并[3,2-b]呋喃的 C-Br 键的进一步官能化。

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

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.