Kinetic resolution in asymmetric epoxidation using iminium salt catalysis

Philip C Bulman Page; Louise F Appleby; Yohan Chan; David P Day; Benjamin R Buckley; Alexandra M Z Slawin; Steven M Allin; Michael J McKenzie

doi:10.1021/jo401345m

Kinetic resolution in asymmetric epoxidation using iminium salt catalysis

J Org Chem. 2013 Aug 16;78(16):8074-82. doi: 10.1021/jo401345m. Epub 2013 Aug 6.

Authors

Philip C Bulman Page¹, Louise F Appleby, Yohan Chan, David P Day, Benjamin R Buckley, Alexandra M Z Slawin, Steven M Allin, Michael J McKenzie

Affiliation

¹ School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, Norfolk NR4 7TJ, UK. p.page@uea.ac.uk

Abstract

The first reported examples of kinetic resolution in epoxidation reactions using iminium salt catalysis are described, providing up to 99% ee in the epoxidation of racemic cis-chromenes.

Publication types

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

MeSH terms

Catalysis
Epoxy Compounds / chemical synthesis*
Epoxy Compounds / chemistry
Imines / chemistry*
Kinetics
Molecular Conformation
Salts / chemistry
Stereoisomerism

Substances

Epoxy Compounds
Imines
Salts