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https://doi.org/10.1021/jo0200421
DC Field | Value | |
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dc.title | 1,2-dioxines as masked Cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones | |
dc.contributor.author | Greatrex, B.W. | |
dc.contributor.author | Kimber, M.C. | |
dc.contributor.author | Taylor, D.K. | |
dc.contributor.author | Fallon, G. | |
dc.contributor.author | Tiekink, E.R.T. | |
dc.date.accessioned | 2014-10-16T08:18:02Z | |
dc.date.available | 2014-10-16T08:18:02Z | |
dc.date.issued | 2002-07-26 | |
dc.identifier.citation | Greatrex, B.W., Kimber, M.C., Taylor, D.K., Fallon, G., Tiekink, E.R.T. (2002-07-26). 1,2-dioxines as masked Cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones. Journal of Organic Chemistry 67 (15) : 5307-5314. ScholarBank@NUS Repository. https://doi.org/10.1021/jo0200421 | |
dc.identifier.issn | 00223263 | |
dc.identifier.uri | http://scholarbank.nus.edu.sg/handle/10635/92896 | |
dc.description.abstract | Addition 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.description.uri | http://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1021/jo0200421 | |
dc.source | Scopus | |
dc.type | Article | |
dc.contributor.department | CHEMISTRY | |
dc.description.doi | 10.1021/jo0200421 | |
dc.description.sourcetitle | Journal of Organic Chemistry | |
dc.description.volume | 67 | |
dc.description.issue | 15 | |
dc.description.page | 5307-5314 | |
dc.description.coden | JOCEA | |
dc.identifier.isiut | 000176918900032 | |
Appears in Collections: | Staff Publications |
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