Access to (E)-δ-Vinyl-Homoallylic Alcohols/Ethers/Pyrazoles by Ring-opening Nucleophilic Substitution of cyclopropyl allylic alcohols

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-05-24 DOI:10.1039/d5qo00678c

Yulu Zhang, Ying Shao, Jiangtao Sun, Shengbiao Tang

引用次数: 0

Abstract

A highly efficient Lewis acid-catalyzed ring-opening nucleophilic substitution of cyclopropyl allylic alcohols has been developed. The use of pyrazoles as nucleophiles, under catalysis with Yb(OTf)3, a series of (E)-δ-vinyl-homoallylic pyrazoles were obtained in moderate to good yields. When the use of water or alcohols as nucleophiles, under the catalyst of Ga(OTf)3, the desired (E)-δ-Vinyl-homoallylic alcohols/ethers were achieved. The cyclopropyl allylic alcohols have been successfully employed for the first time in ring-opening nucleophilic substitution reactions. This method features mild condition, good functional group tolerance.

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环丙基烯丙醇开环亲核取代制备(E)-δ-乙烯基均烯丙醇/醚/吡唑

研究了一种高效的路易斯酸催化环丙基烯丙醇开环亲核取代反应。以吡唑为亲核试剂，在Yb(OTf)3的催化下，以中高收率合成了一系列(E)-δ-乙烯基-均烯丙基吡唑。当以水或醇为亲核试剂时，在Ga(OTf)3的催化下，可以得到所需的(E)-δ-乙烯基均烯丙基醇/醚。首次成功地将环丙基烯丙醇用于开环亲核取代反应中。该方法条件温和，官能团耐受性好。

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 Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.