[3, 3]‐Sigmatropic Rearrangement of Cyclopropenylcarbinyl Cyanates: Access to Alkylidene(aminocyclopropane) Derivatives. Issue 56 (10th September 2018)

• Record Type: Journal Article
• Authors: Ernouf, Guillaume; Brayer, Jean‐Louis; Folléas, Benoît; Demoute, Jean‐Pierre; Meyer, Christophe; Cossy, Janine
• Is Part Of: Chemistry. Volume 24:Issue 56(2018)
• Page Start: 15104
• Page End: 15111
• Publication Date: 2018-09-10
• Subjects: cyanates -- isocyanates -- sigmatropic rearrangement -- strained rings -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201803231
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Cyclopropenylcarbinyl cyanates, generated in situ by dehydration of the corresponding carbamates, underwent an efficient and stereoselective [3, 3]‐sigmatropic rearrangement leading to the corresponding alkylidene(isocyanatocyclopropanes), which could be converted into various alkylidene(aminocyclopropane) derivatives in a one‐pot manner. This transformation complements the repertoire of sigmatropic rearrangements involving cyclopropenylcarbinol derivatives and in particular, the previously reported Overman rearrangement of cyclopropenylcarbinyl trichloroacetimidates. Abstract : Cyclopropenylcarbinyl cyanates, generated in situ by dehydration of the corresponding carbamates, undergo an efficient and stereoselective [3, 3]‐sigmatropic rearrangement leading to the corresponding alkylidene(isocyanatocyclopropanes) that can be readily converted into various alkylidene(aminocyclopropane) derivatives in a one‐pot manner.