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

2-Acetylcyclopentanone undergoes a smooth reaction with triphenylphosphine and dialkyl acetylenedicarboxylates to produce dialkyl 2-(1-acetyl-2-oxocyclopentyl)-3-(1,1,1-triphenyl-λ(5)-phosphanylidene)succinates. These compounds undergo intra-molecular Wittig reactions in boiling benzene to produce h...

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Detalles Bibliográficos
Autores principales: Asghari, Sakineh, Poushani, Mohammad Bagher, Ramezani, Samaneh
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2008
Materias:
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Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6245385/
https://www.ncbi.nlm.nih.gov/pubmed/18305421
http://dx.doi.org/10.3390/molecules13020331
Descripción
Sumario:2-Acetylcyclopentanone undergoes a smooth reaction with triphenylphosphine and dialkyl acetylenedicarboxylates to produce dialkyl 2-(1-acetyl-2-oxocyclopentyl)-3-(1,1,1-triphenyl-λ(5)-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.

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