2015 · ORGANIC LETTERS

Synthesis of Functionalized Alkylidenecyclopropanes by Ireland-Claisen Rearrangement of Cyclopropenylcarbinyl Esters

Ernouf, Guillaume, Brayer, Jean-Louis, Folleas, Benoit, Demoute, Jean-Pierre, Meyer, Christophe, Cossy, Janine

Journal
ORGANIC LETTERS
Année
2015
Volume
17
Numéro
15
Pages
3786-3789
Mois
AUG 7
DOI
10.1021/acs.orglett.5b01759

Abstract

Glycolates or glycinates derived from diversely substituted secondary cyclopropenylcarbinols have been involved for the first time in an Ireland-Claisen rearrangement. This reaction allows an efficient and stereoselective access to highly functionalized alkylidenecyclopropanes possessing an alpha-hydroxy or a-amino acid subunit, which in turn are valuable precursors of substituted cyclopropanes by diastereoselective hydrogenation of the exocyclic alkene.

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