155480-22-1Relevant academic research and scientific papers
Stereocontrolled photocyclization of 1,2-diketones: Application of a 1,3-acetyl group transfer methodology to carbohydrates
Herrera, Antonio J.,Rondon, Maria,Suarez, Ernesto
, p. 3384 - 3391 (2008/09/21)
(Chemical Equation Presented) Photolysis of 1-glycosyl-2,3-butanodione 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. Further oxidative opening of the 1-hydroxy-1-methyl-2-cyclobutanone moiety affords new C-ketoside derivatives either in C- and O-glycoside series. This tandem two-step process could be considered to be a stereocontrol led 1,3-transference of an acetyl group, and it can be applied either to pyranose and furanose models.
