First organophosphorus radical-mediated cyclisations to afford medium-sized rings: eight-membered lactones and seven- and eight-membered lactams

[Display omitted] 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-memb...

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Bibliographic Details
Published inTetrahedron letters Vol. 46; no. 23; pp. 4027 - 4030
Main Authors Lang, Stuart, Corr, Michael, Muir, Neil, Khan, Tanweer A., Schönebeck, Franziska, Murphy, John A., Payne, Andrew H., Williams, Andrew C.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.06.2005
Elsevier
Subjects
Chemistry
Chemistry, Organic
Cyclisation
DEPO
EPHP
Phosphorus
Physical Sciences
Radical
Science & Technology
Phosphorus
EPHP
Cyclisation
Radical
DEPO
radical
(ALKOXYCARBONYL)METHYL RADICALS
EFFICIENT ROUTE
AQUEOUS-MEDIA
CARBON BOND FORMATION
KETYL-OLEFIN CYCLIZATION
8-ENDO CYCLIZATION
ESTERS
cyclisation
STEREOSELECTIVE-SYNTHESIS
HYPOPHOSPHITE
phosphorus
WATER
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Summary:[Display omitted] 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.04.032