Enamine oxidations. 2. Selective oxidative cleavage of β,β - disubstituted enamines using alumina supported permanganate. Synthesis of one-carbon dehomologated carbonyl compounds from enamines

✍ Scribed by Clifford E. Harris; William Chrisman; Sally A. Bickford; Lawrence Y. Lee; Antonia E. Torreblanca; Bakthan Singaram

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 202 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02504-x

✦ Synopsis

Treatment of fl, fl -disubstituted enamines with potassium permanganste suppocted on neutral alumina leads to a mild and selective oxidative cleavage reaction which produces ketones and formamides. The ketones can be isolated in high yield and purity by a simple workup procedure. The oxidizing agent is selective and wefermtiaily oxidizes an enamine carbon-carbon double bond in the presence of a distal carbon-carbon double bond. Other functional groups unaffected by this reagent include nitriles, secondary alcohols, and alkynes allowing a wide range of potentially selective oxidations.