In this article the first enantioselective epoxidation reaction of acyclic and cyclic 2-arylidene-1,3-diketones is reported. Easily accessible or commercially available alpha,alpha-diaryl prolinols as the organocatalysts in the presence of tert-butyl hydroperoxide (TBHP) provide the corresponding epoxides in high to excellent yield (up to 99%) and up to 85% ee (ee > 90% after crystallisation). These epoxides are pharmaceutically important building blocks and intermediates for the synthesis of densely functionalised epoxide derivatives.
Asymmetric Epoxidation of 2-Arylidene-1,3-Diketones: Facile Access to Synthetically Useful Epoxides
RUSSO, ALESSIO;LATTANZI, Alessandra
2010-01-01
Abstract
In this article the first enantioselective epoxidation reaction of acyclic and cyclic 2-arylidene-1,3-diketones is reported. Easily accessible or commercially available alpha,alpha-diaryl prolinols as the organocatalysts in the presence of tert-butyl hydroperoxide (TBHP) provide the corresponding epoxides in high to excellent yield (up to 99%) and up to 85% ee (ee > 90% after crystallisation). These epoxides are pharmaceutically important building blocks and intermediates for the synthesis of densely functionalised epoxide derivatives.File in questo prodotto:
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