An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective Rh(II)-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes

Enantioselective quaternary carbon construction in the assembly of cyclopentenones employing a Rh(II)-catalyzed, formal [4+1]-cycloaddition is described. A Rh(2)(S-TCPTTL)(4)-catalyzed cyclopropanation of a vinyl ketene with a disubstituted diazo compound initiates a stereoretentive, accelerated rin...

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Detalles Bibliográficos
Autores principales: Rodriguez, Kevin X., Pilato, Tara C., Ashfeld, Brandon L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5931190/
https://www.ncbi.nlm.nih.gov/pubmed/29844895
http://dx.doi.org/10.1039/c8sc00020d
Descripción
Sumario:Enantioselective quaternary carbon construction in the assembly of cyclopentenones employing a Rh(II)-catalyzed, formal [4+1]-cycloaddition is described. A Rh(2)(S-TCPTTL)(4)-catalyzed cyclopropanation of a vinyl ketene with a disubstituted diazo compound initiates a stereoretentive, accelerated ring expansion to provide the cycloadduct in good to excellent yields and enantioselectivity.

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