Oxidation of Glycals with Hydrogen Peroxide

✍ Scribed by Danuta Mostowicz; Margarita Jurczak; Hans-Jurgen Hamann; Eugen Höft; Marek Chmielewski

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 173 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199811)1998:11<2617::aid-ejoc2617>3.0.co;2-0

✦ Synopsis

Tri-O-acetyl-D-glucal (8) treated with a mixture of hydrogen hydroperoxide. 2,3-Unsaturated anomeric hydroperoxides of αand β-D-erythroand α-D-threo-19, -20, and -24, peroxide-molybdenum trioxide undergoes a Ferrier rearrangement to form 2,3-unsaturated anomeric respectively, were used for the enantioselective epoxidation of prochiral allylic alcohols 25-27 and oxidation of sulfides hydroperoxides 14 and 15.Tri-O-acetyl-D-galactal (10) and tri-O-benzyl-D-glucal (9), under the same conditions, afford 28 and 29 to give stereoselectivities of up to 50% enantiomeric excess. the hydroperoxides in a low yield, whereas tri-O-benzyl-Dgalactal (11) does not produce any unsaturated