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Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid

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dc.contributor.authorBunnage, Mark E.
dc.contributor.authorDavies, Stephen G.
dc.contributor.authorRoberts, Paul M.
dc.contributor.authorSmith, Andrew D.
dc.contributor.authorWithey, Jonathan M.
dc.date.accessioned2015-04-17
dc.date.accessioned2022-05-27T01:13:47Z
dc.date.available2022-05-27T01:13:47Z
dc.date.issued2004
dc.description.abstractThe diastereoselective conjugate addition of lithium (S)-N-benzyl-N-alpha-methylbenzylamide has been successfully applied to the first asymmetric syntheses of cis-(3S,4R)- and trans-(3R,4R)-4-aminotetrahydrofuran-3-carboxylic acids (26% and 25% overall yield respectively, > 98% d.e. and > 97% e. e. in each case). Furthermore, the most efficient asymmetric synthesis to date of cis-( 3R, 4R)- and trans-( 3R, 4S)-4-aminopyrrolidine carboxylic acids is delineated: for cis-( 3R, 4R), four steps, > 98% d.e., 52% overall yield; for trans-( 3R, 4S), five steps, > 98% d.e., 50% overall yield.
dc.description.urihttp://library.macewan.ca/cgi-bin/SFX/url.pl/7LX
dc.format.extent15 kb
dc.identifier.citationBunnage, M., Davies, S., Roberts, P., Smith, A., & Withey, J. (2004). Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid. Organic & Biomolecular Chemistry, 2(19), 2763-2776. doi:10.1039/B407558G
dc.identifier.doihttps://doi.org/10.1039/B407558G
dc.identifier.urihttps://hdl.handle.net/20.500.14078/277
dc.languageEnglish
dc.language.isoen
dc.rightsAll Rights Reserved
dc.subjectbeta-amino acids
dc.subjectinfluenza neuraminidase inhibitors
dc.subjectkinetic resolution
dc.titleAsymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic aciden
dc.typeArticle

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