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Single enantiomer synthesis of alpha-(trifluoromethyl)-beta-lactam

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dc.contributor.authorJurcik, Vaclav
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorO'Hagan, David
dc.date.accessioned2013-12-04T15:01:02Z
dc.date.available2013-12-04T15:01:02Z
dc.date.issued2011-06-06
dc.identifier16811674
dc.identifier0d917110-24be-4c64-b65d-7c96b85b94e6
dc.identifier000291353600001
dc.identifier79958812471
dc.identifier.citationJurcik , V , Slawin , A M Z & O'Hagan , D 2011 , ' Single enantiomer synthesis of alpha-(trifluoromethyl)-beta-lactam ' , Beilstein Journal of Organic Chemistry , vol. 7 , pp. 759-766 . https://doi.org/10.3762/bjoc.7.86en
dc.identifier.issn1860-5397
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56862040
dc.identifier.otherORCID: /0000-0002-0510-5552/work/68281298
dc.identifier.urihttps://hdl.handle.net/10023/4257
dc.description.abstractThe first synthesis of alpha-(trifluoromethyl)-beta-lactam ((S)-1) is reported. The route starts from alpha-(trifluoromethyl)acrylic acid (2). Conjugate addition of alpha-(p-methoxyphenyl)ethylamine ((S)-3b), generated an addition adduct 4b which was cyclised to beta-lactam 5b. Separation of the diastereoisomers by chromatography gave ((alpha S,3S)-5b). N-Debenzylation afforded the desired alpha-(trifluoromethyl)-beta-lactam ((S)-1). The absolute stereochemistry of diastereoisomers 5 was determined by X-ray crystallographic determination of a close structural analogue, (alpha S,3S)-5c, and then H-1 and F-19 NMR correlation to the individual diastereoisomers of 5a and 5b.
dc.format.extent8
dc.format.extent481229
dc.language.isoeng
dc.relation.ispartofBeilstein Journal of Organic Chemistryen
dc.subjectEnantiomeric resolutionen
dc.subjectErganofluorine building blocksen
dc.subjectAlpha-(trifluoromethyl)-beta-lactamen
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titleSingle enantiomer synthesis of alpha-(trifluoromethyl)-beta-lactamen
dc.typeJournal articleen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doi10.3762/bjoc.7.86
dc.description.statusPeer revieweden


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