Me(2)(CH(2)[double bond, length as m-dash]CH)SiCN: a bifunctional ethylene equivalent for Diels–Alder reaction based controllable tandem synthesis

A bifunctional silyl reagent Me(2)(CH(2)[double bond, length as m-dash]CH)SiCN has been developed as a novel ethylene equivalent for the Diels–Alder (DA) reaction. The use of this reagent enables the controllable synthesis of value-added cyclohexenyl ketones or 2-acyl cyclohexancarbonitrile derivati...

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Detalles Bibliográficos
Autores principales: Wu, Wen-Biao, Mu, Bo-Shuai, Yu, Jin-Sheng, Zhou, Jian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8943849/
https://www.ncbi.nlm.nih.gov/pubmed/35432855
http://dx.doi.org/10.1039/d2sc00147k
Descripción
Sumario:A bifunctional silyl reagent Me(2)(CH(2)[double bond, length as m-dash]CH)SiCN has been developed as a novel ethylene equivalent for the Diels–Alder (DA) reaction. The use of this reagent enables the controllable synthesis of value-added cyclohexenyl ketones or 2-acyl cyclohexancarbonitrile derivatives through a five- or six-step tandem sequence based on a Wittig/cyanosilylation/DA reaction/retro-cyanosilylation/isomerization sequence that involves a temporary silicon-tethered intramolecular DA reaction.

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