The first application of cinchona thioureas as organocatalysts in an oxidative process has been disclosed. Specifically, cinchona thioureas/tert-butyl hydroperoxide was found to be an effective system for an unprecedented asymmetric epoxidation of highly challenging deactivated 1,1-disubstituted alkenes. The corresponding terminal epoxides, bearing a quaternary stereogenic center, have been isolated in good to excellent yield (up to 98%) and enantioselectivity (up to 99% ee) by using 5 or 10 mol% of the organocatalyst.

Highly Enantioselective Epoxidation Catalyzed by Cinchona Thioureas: Synthesis of Functionalized Terminal Epoxides Bearing a Quaternary Stereogenic Center

RUSSO, ALESSIO;LATTANZI, Alessandra
2012

Abstract

The first application of cinchona thioureas as organocatalysts in an oxidative process has been disclosed. Specifically, cinchona thioureas/tert-butyl hydroperoxide was found to be an effective system for an unprecedented asymmetric epoxidation of highly challenging deactivated 1,1-disubstituted alkenes. The corresponding terminal epoxides, bearing a quaternary stereogenic center, have been isolated in good to excellent yield (up to 98%) and enantioselectivity (up to 99% ee) by using 5 or 10 mol% of the organocatalyst.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11386/3137378
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