Intramolecular photoreactions of (5S)-5-Oxymethyl-2(5H)-furanones as a tool for the stereoselective generation of diverse polycyclic scaffolds

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(Universitat Autònoma de Barcelona. Servei de Ressonància Magnètica Nuclear)
Alibes, Ramón

(Universitat Autònoma de Barcelona. Departament de Química)
Figueredo Galimany, Marta

(Universitat Autònoma de Barcelona. Departament de Química)

Data:	2015
Resum:	The photoactivated evolution of a series of enantiomerically pure 5-oxymethyl-2(5H)-furanones has been investigated. The observed intramolecular photoreactions have proven to be a straightforward entry to diverse and stereochemically rich fragment-molecules, most of which contain the privileged tetrahydropyran (THP) scaffold. The formation of the THP involves a 1,5-hydrogen atom transfer process, leading to a diradical intermediate that recombines to form a new σ C-C bond. These reactions take place under both sensitized and nonsensitized conditions, and they are highly stereoselective. When the substrate contains an allyl residue, the intramolecular [2 + 2] cycloaddition leading to cyclobutanes competes advantageously. When the substrate contains a THP residue, the cyclization involves the concomitant formation of [6,6]-spiroketals with nonanomeric relationships.
Ajuts:	Ministerio de Economía y Competitividad CTQ2013-41161-R Ministerio de Ciencia e Innovación CTQ2012-32436 Ministerio de Ciencia e Innovación CTQ2010-15380
Drets:	Tots els drets reservats.
Llengua:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Matèria:	Cyclization ; Irradiation ; Ketones ; Lactones ; Mixtures
Publicat a:	Journal of organic chemistry, Vol. 80, issue 19 (Oct. 2015) , p. 9437-9445, ISSN 1520-6904

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Registre creat el 2023-07-11, darrera modificació el 2023-07-23