1,2-dioxines as masked cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones

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dc.contributor.authorGreatrex, B.
dc.contributor.authorKimber, M.
dc.contributor.authorTaylor, D.
dc.contributor.authorFallon, G.
dc.contributor.authorTiekink, E.
dc.date.issued2002
dc.descriptionCopyright © 2002 American Chemical Society
dc.description.abstractAddition of highly stabilized ester nucleophiles to 1,2-dioxines affords good to high yields of γ-lactones with high diastereoselectivity. Heterolytic or homolytic cleavage of the 1,2-dioxines under appropriate conditions generates the key reactive cis γ-hydroxy enones, which ultimately afford the observed γ-lactones. Diastereoselectivity is installed as a result of anti 1,4-addition by the ester enolate to the cis enones followed by intramolecular cyclization. The reaction is tolerant of a range of substitution patterns on the 1,2-dioxine while a broad range of esters are also accommodated. In addition to the synthesis of racemic γ-lactones, highly enantioenriched γ-lactones can also be synthesized when chiral cobalt(II) catalysts are employed for the initial homolytic ring-opening of the 1,2-dioxine.
dc.identifier.citationJournal of Organic Chemistry, 2002; 67(15):5307-5314
dc.identifier.doi10.1021/jo0200421
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.orcidTaylor, D. [0000-0002-3302-4610] [0000-0002-4274-3983] [0000-0003-0633-7424]
dc.identifier.urihttp://hdl.handle.net/2440/4549
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.source.urihttp://pubs.acs.org/cgi-bin/abstract.cgi/joceah/2002/67/i15/abs/jo0200421.html
dc.title1,2-dioxines as masked cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones
dc.title.alternative1,2-dioxines as masked cis gamma-hydroxy enones and their versatility in the synthesis of highly substituted gamma-lactones
dc.typeJournal article
pubs.publication-statusPublished

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