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Enantioselective Epoxidation of α,β-Enones Promoted by α,α-Diphenyl-<scp>l</scp>-prolinol as Bifunctional Organocatalyst

Organic LettersPublished 25 May 2005
Alessandra Lattanzi
Citations136
SJR quartileQ1
SJR score1.24
SNIP1.03

TL;DR

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.

Abstract

[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.

Keywords

Chemistry