79999-45-4Relevant academic research and scientific papers
BORON TRIFLUORIDE-CATALYZED OXIDATION OF GLYCAL ESTERS: AN EFFECTIVE AND MILD METHOD FOR THEIR CONVERSION INTO α,β-UNSATURATED LACTONES
Jarglis, Pan,Lichtenthaler, Frieder W.
, p. 3781 - 3784 (1982)
An effective, one-step procedure for conversion of glycal and 2-acyloxyglycal esters to 2,3-unsaturated lactones has been developed, involving BF3-induced removal of the allylic acyloxy function and oxidation with m-chloroperbenzoic acid or pyridinium chl
InCl3/IBX: A novel reagent system for the conversion of glycals into α,β-unsaturated δ-lactones
Yadav,Reddy, B.V. Subba,Reddy, Ch. Suresh
, p. 4583 - 4585 (2007/10/03)
The combination of indium trichloride with iodoxybenzoic acid (IBX) has been utilized for the first time as a novel reagent system for the one-pot synthesis of 2,3-dideoxy-D-hex-2-enono-1,5-lactones from glycals. The reaction proceeds smoothly in aqueous
Enantiomerically Pure Building Blocks from Sugars, 9. An Expedient Approach to Pyranoid Ene and Enol Lactones by BF3-Catalyzed Peroxidation of Glycal and Hydroxyglycal Esters
Lichtenthaler, Frieder W.,Roenninger, Stephan,Jarglis, Pan
, p. 1153 - 1162 (2007/10/02)
An effective and convenient one-pot procedure, simply involving treatment with boron trifluoride/3-chloroperbenzoic acid (MCPBA), is detailed for the high-yield acquisition of enantiomerically pure dihydropyran-2-ones from mono- and disaccharide-derived glycal and hydroxyglycal esters.An assessment of the scope of the method is given, a total of 17 examples being ample evidence for its preparative utility and apparent generality.Substantiation of the mechanism presented - BF3-promoted removal of the allylic acyloxy group, seizure by MCPBA of the allylcarboxonium ion generated, and fragmentation of the resulting hex-2-enopyranose 1-(3-chloro)perbenzoates on quenching - is provided by characterization of the perester intermediates.Conducting the reaction of glycal esters at room temperature a glycol-type C-1-C-2 bond cleavage occurs instead with the generation of acylated 4,5-dihydroxypentenals.
