Catalytic enantioselective epoxidation of alpha,beta-unsaturated ketones promoted by diaryl-2-pyrrolidinemethanols and tert-butyl hydroperoxide (TBHP) is described. Investigation on structural modifications of the diaryl-2-pyrrolidinemethanols showed that fine tuning of the stereoelectronics of the substituents on the aryl moiety is important to achieve high efficiency. By employing a structurally optimized organocatalyst, significantly reduced loading (10 mol %) can be used to produce the epoxides in high yield and up to 90% ee at room temperature.
Diaryl-2-pyrrolidinemethanols catalyzed enantioselective epoxidation of A,B-enones: new insight into the effect of structural modification of the catalyst on reaction efficiency
LATTANZI, Alessandra;RUSSO, ALESSIO
2006
Abstract
Catalytic enantioselective epoxidation of alpha,beta-unsaturated ketones promoted by diaryl-2-pyrrolidinemethanols and tert-butyl hydroperoxide (TBHP) is described. Investigation on structural modifications of the diaryl-2-pyrrolidinemethanols showed that fine tuning of the stereoelectronics of the substituents on the aryl moiety is important to achieve high efficiency. By employing a structurally optimized organocatalyst, significantly reduced loading (10 mol %) can be used to produce the epoxides in high yield and up to 90% ee at room temperature.File in questo prodotto:
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