Improved enantioselectivity in the epoxidation of cinnamic acid derivatives with dioxiranes from keto bile acids

Olga Bortolini; Giancarlo Fantin; Marco Fogagnolo; Roberto Forlani; Silvia Maietti; Paola Pedrini

doi:10.1021/jo020146b

Improved enantioselectivity in the epoxidation of cinnamic acid derivatives with dioxiranes from keto bile acids

J Org Chem. 2002 Aug 9;67(16):5802-6. doi: 10.1021/jo020146b.

Authors

Olga Bortolini¹, Giancarlo Fantin, Marco Fogagnolo, Roberto Forlani, Silvia Maietti, Paola Pedrini

Affiliation

¹ Università di Ferrara, Dipartimento di Chimica, Via Borsari 46, 44100 Ferrara, Italy. brl@unife.it

PMID: 12153284
DOI: 10.1021/jo020146b

Abstract

The asymmetric epoxidation of substituted cinnamic acids has been obtained in the presence of different keto bile acid derivatives as optically active carbonyl inducers and Oxone as oxygen source. Predominant or almost exclusive formation of both enantiomeric epoxides is obtained (ee up to 95%) depending on the specific substitution at carbons C(7) and C(12) of the bile acid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bile Acids and Salts*
Cinnamates / chemical synthesis*
Cinnamates / chemistry
Epoxy Compounds*
Indicators and Reagents
Ketones
Magnetic Resonance Spectroscopy
Molecular Conformation
Stereoisomerism
Structure-Activity Relationship

Substances

Bile Acids and Salts
Cinnamates
Epoxy Compounds
Indicators and Reagents
Ketones