Photoinduced (4 + 2) Annulation of ortho-Hydroxyphenyl-Substituted para-Quinone Methides with Diazocarbonyls: Diastereodivergent Synthesis of 4-Aryl-dihydrocoumarins

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI:10.1021/acs.orglett.6c02908

Ke-Yin Yu, Xin-Yu Liu, Yu-Han Yang, Wenji Wang, Xian-Tao An, Jiwen Zhang, Chun-An Fan

引用次数: 0

Abstract

A novel photoinduced (4 + 2) annulation of o-hydroxyphenyl-substituted p-quinone methides with diazocarbonyls, chemically initiated by a photochemical Wolff rearrangement, is described. Remarkably, the diastereoselectivity of this reaction can be switched by employing either TBAB/CaH₂ or H₂O as an additive, establishing an effective diastereodivergent approach to synthetically important functionalized 4-aryl-dihydrocoumarins.

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邻羟基苯基取代对醌甲醚与重氮羰基的光诱导（4 + 2）环化：4-芳基二氢香豆素的非对映发散合成

摘要本文描述了一种新的光诱导（4 + 2）邻羟基苯基取代对醌类化合物与重氮羰基的环化反应，该反应是由光化学Wolff重排引发的。值得注意的是，该反应的非对映选择性可以通过TBAB/CaH2或H2O作为添加剂来改变，从而建立了一种有效的非对映发散方法来合成重要的功能化4-芳基二氢香豆素。

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

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.