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
2012-01-01
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.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
