66684-75-1Relevant articles and documents
Divergent Rearrangements of Vinylcyclopropane into Skipped Diene and Cyclopentene: Mechanism, Scope, and Limitations
Delbrassinne, Arnaud,Richald, Maximilien,Janssens, Julien,Robiette, Rapha?l
supporting information, p. 2862 - 2868 (2021/06/11)
Vinylcyclopropanes are versatile intermediates in organic synthesis which undergo various rearrangements. We report a new rearrangement of vinylcyclopropane into skipped diene. A detailed mechanistic study revealed that this transformation involves regioselective ring-opening of the cyclopropane ring followed by 1,2-migration of one of the cyclopropane substituents. Interestingly, our investigations showed that skipped diene is the kinetic product of the process but formation of a more stable cyclopentene is also accessible. The fundamental understanding of the processes involved enabled the development of divergent methodologies allowing to obtain cyclopentene or skipped diene from vinylcyclopropane in a selective and controlled manner.
Palladium-Catalyzed Asymmetric 1,6-Addition of Diarylphosphines to Allylidenemalonates for Chiral Phosphine Synthesis
Wei, Xu,Lu, Junzhu,Duan, Wei-Liang
supporting information, p. 4155 - 4160 (2016/11/26)
A pincer-palladium-catalyzed asymmetric 1,6-addition of diarylphosphines to allylidenemalonates has been developed for the synthesis of chiral allylic phosphines with up to 89% ee under mild conditions.
Organocatalytic asymmetric annulation of 1,3-bis(alkoxycarbonyl)buta-1,3- dienes and aldehydes
Pezzati, Bernardo,Chellat, Mathieu F.,Murphy, John J.,Besnard, Celine,Reginato, Gianna,Stephens, John C.,Alexakis, Alexandre
supporting information, p. 2950 - 2953 (2013/07/26)
Asymmetric organocatalytic annulation of E/Z isomeric mixtures of bis(alkyl carboxylate)buta-1,3-dienes and aldehydes has been realized via enamine catalysis. In the presence of α,α-diphenyl-2-pyrrolidinemethanol trimethylsilyl ether, excellent stereo- and enantioselectivities were achieved for a broad spectrum of substrates.