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First organophosphorus radical-mediated cyclisations to afford medium-sized rings: eight-membered lactones and seven- and eight-membered lactams
Authors:Stuart Lang  Neil Muir  Franziska Schönebeck  Andrew H Payne
Institution:a Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow G1 1XL, UK
b GlaxoSmithKline New Frontiers Science Park, Third Avenue, Harlow, Essex CM 19 5AW, UK
c Eli Lilly and Company Ltd, Lilly Research Centre, Erl Wood Manor, Sunninghill Road, Windlesham, Surrey GU20 6PH, UK
Abstract:The phosphorus based radical precursors N-ethylpiperidine hypophosphite (EPHP) and diethylphosphine oxide (DEPO) are efficient reagents for carrying out the formation of seven- and eight-membered rings. Esters and amides were successfully converted into the corresponding eight-membered lactones and seven- and eight-membered lactams in good to excellent yields.
Keywords:Radical  Phosphorus  DEPO  EPHP  Cyclisation
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