A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl(E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates

Molecules

Sakineh Asghari¹  Mohammad Bagher Poushani² 

[1] Chemistry, University of Mazandaran, P. O. Box 453, Babolsar, Iran E-mails

关键词: phosphorus ylides;    spirocompounds;    intramolecular Wittig reaction;   

DOI  :  10.3390/molecules13020331

来源: mdpi

【 摘 要 】

2-Acetylcyclopentanone undergoes a smooth reaction with triphenylphosphine and dialkyl acetylenedicarboxylates to produce dialkyl 2-(1-acetyl-2-oxocyclopentyl)-3-(1,1,1-triphenyl-λ⁵-phosphanylidene)succinates. These compounds undergo intra-molecular Wittig reactions in boiling benzene to produce highly strained spirocyclobutene derivatives, which spontaneously undergo ring-opening reactions to produce dialkyl (E)-2-[1-(2-oxocyclopentyliden)ethyl]-2-butenedioates.

【 授权许可】

Unknown   
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