Asymmetric epoxidation of 2-arylidene-1,3-diketones: facile access to synthetically useful epoxides.
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.
Russo
Alessio
A
Dipartimento di Chimica, Università di Salerno, Via Ponte don Melillo, 84084, Fisciano, Italy.
Lattanzi
Alessandra
A
D004852:Epoxy Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure
D004852:Epoxy Compounds; D007659:Ketones