Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada.
Chem Rev. 2021 Jan 13;121(1):3-79. doi: 10.1021/acs.chemrev.0c00346. Epub 2020 Oct 21.
The carbon-carbon (C-C) bond cleavage of cyclopropanols is a wide area of research with much current activity. This review highlights new developments in this area over the past two decades. A summary is made of the three main reactivity modes, namely, homoenolate chemistry, β-keto radical chemistry, and acid-catalyzed ring-opening, as well as all other methods for the C-C bond cleavage and functionalization of cyclopropanols, including base-mediated ring-opening, metal-catalyzed C-C insertions and eliminations, oxidative fragmentation using hypervalent iodine reagents, reactions of donor-acceptor cyclopropanols, and pericylic reactions. Emphasis is placed on the synthetic utility of cyclopropanols and related derivatives, which have emerged as unique three-carbon synthons.
环丙醇的 C-C 键断裂是一个广泛的研究领域，目前有很多研究活动。这篇综述重点介绍了过去二十年来该领域的新发展。总结了三种主要的反应模式，即偕羟肟酸化学、β-酮基自由基化学和酸催化的开环，以及环丙醇 C-C 键断裂和官能化的所有其他方法，包括碱介导的开环、金属催化的 C-C 插入和消除、高价碘试剂的氧化断裂、给体-受体环丙醇的反应和周环反应。强调了环丙醇及其相关衍生物的合成实用性，它们已成为独特的三碳合成子。
