The polyamino acid catalysed asymmetric epoxidation of chalcones, discovere
d by Julia and Colonna ct al., provides the epoxides in excellent yields an
d enantioselectivities, but the long reaction times lead to degradation of
the polymer.(1,3).
Lantos et al, used the triphasic polyamino acid catalysed epoxidation for t
he synthesis of the leukotriene antagonist SK&F 104353 in 82% yield and 95%
ec. After Baeyer-Villiger oxidation, recrystallisation and highly regiosel
ective opening of the epoxide with methyl 3-mercaptopropionate, the target
molecule was obtained in >99.5% ee.(5).
Roberts et al. described the preparation of diltiazem, a blood pressure low
ering agent starting from a simple enone precursor via a similar epoxidatio
n/Baeyer-Villiger oxidation/epoxide opening protocol.(6).