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Stereoselective Synthesis of Tri- and Tetrasubstituted Olefins via 1,6-Additions of Diazo Compounds and Their Precursors to p-Quinone Methides

[Image: see text] Reactions of para-quinone methides (p-QMs) with α-diazo-β-ketosulfones and their corresponding esters as well as simple β-dicarbonyl compounds and β-ketosulfones have been carried out under basic conditions. While the reaction of diazosulfone with p-QMs afforded trisubstituted olef...

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Detalles Bibliográficos
Autores principales: Pati, Soumyaranjan, Rayi, Soniya, Namboothiri, Irishi N. N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9954373/
https://www.ncbi.nlm.nih.gov/pubmed/36855755
http://dx.doi.org/10.1021/acsorginorgau.1c00012
Descripción
Sumario:[Image: see text] Reactions of para-quinone methides (p-QMs) with α-diazo-β-ketosulfones and their corresponding esters as well as simple β-dicarbonyl compounds and β-ketosulfones have been carried out under basic conditions. While the reaction of diazosulfone with p-QMs afforded trisubstituted olefins via deacylative 1,6-addition and elimination, α-diazo-β-ketoesters and various active methylene compounds such as 1,3-dicarbonyls and β-ketosulfones afforded tetrasubstituted olefins via 1,6-addition and aerial oxidation. These simple, environmentally benign, and mechanistically diverse protocols provided the products in moderate to excellent yields and selectivities.