Jennings, WB,Schweppe, A,Testa, LM,Zaballos-Garcia, E,Sepulveda-Arques, J;

2003

January

Synlett

Applications of N-phosphinoyloxaziridines in the conversion of alkenes to epoxides and esters to alpha-hydroxyesters

Validated

()

oxaziridines alpha-hydroxyesters epoxidation enolate oxidation stereoselective oxidation ASYMMETRIC-SYNTHESIS ACIDS

121

123

N-Phosphinoyloxaziridines possessing an activating 3-CF3 substituent oxidise alkenes to epoxides at 35-45degreesC. Esters can be oxidised to alpha-hydroxyesters via their lithium enolates by various 3-subsituted N-phosphinoyloxaziridines. Stereoselectivity is observed in both these oxidations.