利用位阻克服策略对映选择性合成高功能化2,3-二氢苯并呋喃衍生物。

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-06-06 DOI:10.1021/acs.joc.5c00764

Dong-Qun Huang, Shi-Ying Wu, Hui Zhang, Jian-Qiang Zhao, Yong You, Yan-Ping Zhang, Lei Yang, Zhen-Hua Wang, Wei-Cheng Yuan

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引用次数: 0

摘要

对醌单亚胺的不对称环加成反应是构建苯并杂环的重要研究热点。然而，由于空间位阻效应，在高度空间位阻位点实现高效的环加成具有挑战性，但具有实际价值。本文通过位阻克服策略，建立了对醌单亚胺与1-乙烯基萘-2-醇和3-乙烯基吲哚的不对称[3 + 2]环加成反应。二萘基手性磷酸催化不对称环加成反应，合成高官能化2,3-二氢苯并呋喃，收率一般较高，具有良好的立体选择性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Enantioselective Synthesis of Highly Functionalized 2,3-Dihydrobenzofuran Derivatives via Steric Hindrance-Overcoming Strategy.

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Enantioselective Synthesis of Highly Functionalized 2,3-Dihydrobenzofuran Derivatives via Steric Hindrance-Overcoming Strategy.

The asymmetric cycloaddition reaction of p-quinone monoimides is a significant research focus for constructing benzofused heterocycles. However, due to steric effects, achieving efficient cycloaddition at highly sterically hindered site is challenging but practically valuable. Herein, we develop an asymmetric [3 + 2] cycloaddition reaction of p-quinone monoimides with 1-vinylnaphthalen-2-ols and 3-vinylindoles via steric hindrance-overcoming strategy. Binaphthalene-based chiral phosphoric acid catalyzes the asymmetric cycloaddition reaction to synthesize highly functionalized 2,3-dihydrobenzofurans in generally good yields with good to excellent stereoselectivities.

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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.