Sigmatropic rearrangements of cyclopropenylcarbinol derivatives. Access to diversely substituted alkylidenecyclopropanes.
alkylidenecyclopropanes
cyclopropanes
cyclopropenes
sigmatropic rearrangements
strained rings
Journal
Beilstein journal of organic chemistry
ISSN: 1860-5397
Titre abrégé: Beilstein J Org Chem
Pays: Germany
ID NLM: 101250746
Informations de publication
Date de publication:
2019
2019
Historique:
received:
22
10
2018
accepted:
08
01
2019
entrez:
26
2
2019
pubmed:
26
2
2019
medline:
26
2
2019
Statut:
epublish
Résumé
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.
Identifiants
pubmed: 30800182
doi: 10.3762/bjoc.15.29
pmc: PMC6369978
doi:
Types de publication
Journal Article
Review
Langues
eng
Pagination
333-350Références
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