Tetrahedron Letters p. 981 - 984 (1997)
Update date:2022-08-17
Topics:
Harris, Clifford E.
Chrisman, William
Bickford, Sally A.
Lee, Lawrence Y.
Torreblanca, Antonia E.
Singaram, Bakthan
Treatment of β,β-disubstituted enamines with potassium permanganate supported 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 preferentially 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.
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