25364-76-5Relevant articles and documents
Palladium-Catalyzed Asymmetric 1,6-Addition of Diarylphosphines to Allylidenemalonates for Chiral Phosphine Synthesis
Wei, Xu,Lu, Junzhu,Duan, Wei-Liang
, p. 4155 - 4160 (2016)
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.
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.
Ring-Opening of Vinylcyclopropane-1,1-dicarboxylates by Boronic Acids under Ligandless Palladium Catalysis in Neat Water
Yin, JieXiang,Hyland, Christopher J. T.
, p. 6529 - 6536 (2015/10/06)
We report a highly efficient ring-opening reaction of vinylcyclopropanes by boronic acids in water, using palladium nanoparticles formed from Pd(OAc)2 under ligandless conditions. Unsubstituted vinylcyclopropanes provide linear addition products with high selectivity, while a switch in regioselectivity to branched products is observed for aryl-substituted vinylcyclopropanes.