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不对称合成环丙醇中间体的最新进展。

Recent advances in asymmetric synthesis cyclopropanol intermediates.

作者信息

Laktsevich-Iskryk Marharyta, Hurski Alaksiej, Ošeka Maksim, Kananovich Dzmitry

机构信息

Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618, Tallinn, Estonia.

Republican Scientific Center of Human Issues, Belarusian State University, Minsk 220064, Belarus.

出版信息

Org Biomol Chem. 2025 Jan 29;23(5):992-1015. doi: 10.1039/d4ob01746c.

DOI:10.1039/d4ob01746c
PMID:39670922
Abstract

Cyclopropanols have attracted significant attention in organic synthesis as versatile three-carbon synthons, as this readily available class of donor-activated cyclopropanes undergoes miscellaneous transformations, either ring-opening or with retention of the cyclopropane ring. This review summarizes stereoselective and stereoretentive transformations suitable for asymmetric synthesis. The utility of cyclopropanols is discussed for two main strategies: (i) substrate-controlled transformations using enantiomerically enriched cyclopropanol intermediates through a traditional approach, and (ii) the use of nonchiral or racemic cyclopropanols, where asymmetric induction is achieved through a chiral catalyst, representing a direction that has recently emerged.

摘要

环丙醇作为通用的三碳合成子在有机合成中引起了广泛关注,因为这类易于获得的供体活化环丙烷会发生各种转化,包括开环或保留环丙烷环。本综述总结了适用于不对称合成的立体选择性和立体保持性转化。讨论了环丙醇在两种主要策略中的应用:(i) 通过传统方法使用对映体富集的环丙醇中间体进行底物控制的转化,以及 (ii) 使用非手性或外消旋环丙醇,其中通过手性催化剂实现不对称诱导,这代表了最近出现的一个方向。

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