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Título

Stereocontrolled Photocyclization of 1,2-Diketones Applied to Carbohydrate Models: A New Entry to C-Ketosides

AutorHerrera, Antonio J. ; Rondón, María ; Suárez, Ernesto
Palabras clavePhotochemistry
Spiro compounds
Memory effect
Diastereoselectivity
Glycosides
Fecha de publicación25-jun-2007
EditorThieme
CitaciónSynlett 12: 1851-1856 (2007)
ResumenPhotolysis of 1-glycosyl-2,3-butanedione derivatives ­using visible light is a mild and selective procedure for the synthesis of chiral 1-hydroxy-1-methyl-5-oxaspiro[3.5]nonan-2-one carbohydrate derivatives. The results strongly suggest that stereocontrol of the cyclization is dependent on conformational and stereoelectronic factors which can be modulated efficiently by using photosensitizers in some cases. Further oxidative opening of the 1-hydroxy-1-methyl-2-cyclobutanone moiety affords new C-ketoside derivatives. This two-step process could be considered to be a ­stereocontrolled 1,3-transfer of an acetyl group.
Descripción7 pages, 1 table, 2 schemes.-- Printed version published Jul 2007.
Versión del editorhttp://dx.doi.org/10.1055/s-2007-984523
URIhttp://hdl.handle.net/10261/12980
DOI10.1055/s-2007-984523
ISSN0936-5214
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