Highly Efficient Hydroxylation of Carbonyl Compounds with Dimethyldioxirane

✍ Scribed by Adam, Waldemar ;Prechtl, Frank

• Publisher: Wiley (John Wiley & Sons)
• Year: 1991
• Tongue: English
• Weight: 485 KB
• Volume: 124
• Category: Article
• ISSN: 0009-2940
• DOI: 10.1002/cber.19911241034

✦ Synopsis

The enolates and/or enols of ketones, esters, P-diketones, P-0x0 esters, and p-0x0 lactones were transformed by dimethyldioxirane (isolated in acetone solution or generated in situ) into their a-hydroxy compounds in good to excellent yields. The direct hydroxylation of the enols was significantly en-hanced by the use of fluoride ion. For the enolate of camphor the exolendo diastereoselectivity depended significantly on the metal ligand; the highest exo/endo ratio (93:7) was observed for the enol trimethylsilyl ether of camphor.