Highly enantioselective epoxidation of alpha, beta-unsaturated esters by chiral dioxirane.
This paper describes a highly enantioselective epoxidation of alpha,beta-unsaturated esters using the fructose-derived ketone 2 as catalyst and Oxone as oxidant. High ee's have been obtained for a number of trans and trisubstituted substrates (82-98% ee). The results described show that it is feasible for dioxiranes to effectively epoxidize electron-deficient olefins with high ee's.
Wu
Xin-Yan
XY
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
She
Xuegong
X
Shi
Yian
Y
D002934:Cinnamates / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D013237:Stereoisomerism; D013464:Sulfuric Acids / Q000737:chemistry
D002934:Cinnamates; D004852:Epoxy Compounds; D007659:Ketones; D013464:Sulfuric Acids; C061799:dioxirane; C048813:potassium peroxymonosulfuric acid