Oxidative radical cyclisations for the synthesis of gamma-lactones.
The use of manganese(III) acetate in combination with copper(II) triflate allows the synthesis of [3.3.0]-bicyclic gamma-lactones from 4-pentenylmalonates in excellent yields.
Powell
Luke H
LH
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UKCB2 1EW.
Docherty
Paul H
PH
Hulcoop
David G
DG
Kemmitt
Paul D
PD
Burton
Jonathan W
JW
D000085:Acetates / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008314:Malonates / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction
D000085:Acetates; D019086:Bridged Bicyclo Compounds, Heterocyclic; D003517:Cyclopentanes; D005609:Free Radicals; D007783:Lactones; D008314:Malonates; D008698:Mesylates; D009942:Organometallic Compounds; C521134:manganese(III) acetate dihydrate; D003300:Copper; C012077:trifluoromethanesulfonic acid