Manganese(III) acetate mediated oxidative radical cyclizations. Toward vicinal all-carbon quaternary stereocenters

Angus W J Logan; Jeremy S Parker; Michal S Hallside; Jonathan W Burton

doi:10.1021/ol300625u

Manganese(III) acetate mediated oxidative radical cyclizations. Toward vicinal all-carbon quaternary stereocenters

Org Lett. 2012 Jun 15;14(12):2940-3. doi: 10.1021/ol300625u. Epub 2012 Jun 4.

Authors

Angus W J Logan¹, Jeremy S Parker, Michal S Hallside, Jonathan W Burton

Affiliation

¹ Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK.

PMID: 22662754
DOI: 10.1021/ol300625u

Abstract

Manganese(III) acetate mediated oxidative radical cyclizations have been used to synthesize a range of densely functionalized and sterically congested cyclopentane-lactones. A number of the resulting lactones contain vicinal all-carbon quaternary stereocenters adjacent to a tertiary benzylic stereocenter and are formed with high levels of stereocontrol.

Publication types

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

MeSH terms

Acetates / chemistry*
Carbon / chemistry*
Cyclization
Free Radicals / chemistry
Models, Molecular
Molecular Structure
Organometallic Compounds / chemistry*
Oxidation-Reduction
Stereoisomerism

Substances

Acetates
Free Radicals
Organometallic Compounds
manganese(III) acetate dihydrate
Carbon