Ernouf Guillaume, Brayer Jean-Louis, Meyer Christophe, Cossy Janine
Laboratory of Organic Chemistry, Institute of Chemistry, Biology, Innovation (CBI), ESPCI Paris, CNRS (UMR 8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Minakem, Parc Naturel Régional Scarpe-Escaut, 145 chemin des lilas, 59310 Beuvry-la-Forêt, France.
Beilstein J Org Chem. 2019 Feb 5;15:333-350. doi: 10.3762/bjoc.15.29. eCollection 2019.
Cyclopropenes constitute useful precursors of other classes of compounds incorporating a three-membered ring. Although the transformation of substituted cyclopropenes into alkylidenecyclopropanes can be accomplished through different strategies, this review is focusing specifically on the use of [2,3]- and [3,3]-sigmatropic rearrangements involving cyclopropenylcarbinol derivatives as substrates. These sigmatropic rearrangements, which have been developed in recent years, allow a remarkably efficient and stereoselective access to a wide variety of heterosubstituted and/or functionalized alkylidenecyclopropanes which would not be readily accessible by other strategies. The different [2,3]- and [3,3]-sigmatropic rearrangements of cyclopropenylcarbinol derivatives disclosed to date, as well as the analysis of their substrate scope and some applications of the products arising from those reactions, are presented in this review.
环丙烯是构成含三元环的其他各类化合物的有用前体。虽然取代环丙烯向亚烷基环丙烷的转化可通过不同策略实现，但本综述特别关注以环丙烯基甲醇衍生物为底物的[2,3]-和[3,3]-σ迁移重排的应用。这些近年来发展起来的σ迁移重排，能以显著高效且立体选择性的方式合成多种杂取代和/或官能化的亚烷基环丙烷，而这些化合物通过其他策略难以轻易获得。本综述介绍了迄今为止所披露的环丙烯基甲醇衍生物的不同[2,3]-和[3,3]-σ迁移重排，以及对其底物范围的分析和这些反应产物的一些应用。
