Asymmetric epoxidation of trans-chalcones organocatalyzed by beta-amino alcohols

作者：Russo Alessio; Lattanzi Alessandra^*

来源：European Journal of Organic Chemistry, 2008, (16): 2767-2773.

DOI：10.1002/ejoc.200800140

• asymmetric synthesis
• epoxidation
• organocatalysis
• amino alcohols

Cyclic and acyclic beta-amino alcohols were examined as organocatalysts in the epoxidation of trans-chalcones with tertbutyl hydroperoxide as the oxidant. Primary, secondary, and tertiary P-amino alcohols are able to promote the reaction with variable activity and level of asymmetric induction. Subtle modifications to the structures of simple primary P-amino alcohol strongly influenced their efficiency in the epoxidation. They are promising catalysts that afford trans-chalcone epoxides in up to 52 % ee at room temperature.

• 出版日期2008-6