Enantioselective epoxidation of alpha,beta-enones promoted by alpha,alpha-diphenyl-L-prolinol as bifunctional organocatalyst.
[reaction: see text] An operationally simple and mild protocol for the catalytic enantioselective epoxidation of alpha,beta-unsaturated ketones has been estabilished using commercially available alpha,alpha-diphenyl-l-prolinol as bifunctional organocatalyst and tert-butyl hydroperoxide (TBHP) as oxidant. The epoxides have been obtained in good yields and with up to 80% ee.
Lattanzi
Alessandra
A
Dipartimento di Chimica, Università di Salerno, Via S. Allende, I-84081 Baronissi, Salerno, Italy. lattanzi@unisa.it
D001713:Biphenyl Compounds / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
D001713:Biphenyl Compounds; D004852:Epoxy Compounds; D007659:Ketones; D011759:Pyrrolidines; C010574:biphenyl; C010509:prolinol