Please use this identifier to cite or link to this item: https://scholarbank.nus.edu.sg/handle/10635/93782
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dc.titleExpanding the utility of Brønsted base catalysis: Biomimetic enantioselective decarboxylative reactions
dc.contributor.authorPan, Y.
dc.contributor.authorKee, C.W.
dc.contributor.authorJiang, Z.
dc.contributor.authorMa, T.
dc.contributor.authorZhao, Y.
dc.contributor.authorYang, Y.
dc.contributor.authorXue, H.
dc.contributor.authorTan, C.-H.
dc.date.accessioned2014-10-16T08:28:21Z
dc.date.available2014-10-16T08:28:21Z
dc.date.issued2011-07-18
dc.identifier.citationPan, Y., Kee, C.W., Jiang, Z., Ma, T., Zhao, Y., Yang, Y., Xue, H., Tan, C.-H. (2011-07-18). Expanding the utility of Brønsted base catalysis: Biomimetic enantioselective decarboxylative reactions. Chemistry - A European Journal 17 (30) : 8363-8370. ScholarBank@NUS Repository.
dc.identifier.issn09476539
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/93782
dc.description.abstractAs a result of the low reactivity of simple esters, the use of them as nucleophiles in direct asymmetric transformations is a long-standing challenge in synthetic organic chemistry. Nature approaches this difficulty through a decarboxylative mechanism, which is used for polyketide synthesis. Inspired by nature, we report guanidine-catalyzed biomimetic decarboxylative C-C and C-N bond-formation reactions. These highly enantioselective decarboxylative Mannich and amination reactions utilized malonic acid half thioesters as simple ester surrogates. It is proposed that nucleophilic addition precedes decarboxylation in the mechanism, which has been investigated in detail through the identification of intermediates by using electrospray ionization (ESI) mass-spectrometric analysis and DFT calculations. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
dc.description.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1002/chem.201100687
dc.sourceScopus
dc.subjectamination
dc.subjectbiomimetic synthesis
dc.subjectdecarboxylation
dc.subjectdensity functional calculations
dc.subjectMannich reaction
dc.subjectorganocatalysis
dc.typeArticle
dc.contributor.departmentCHEMISTRY
dc.description.sourcetitleChemistry - A European Journal
dc.description.volume17
dc.description.issue30
dc.description.page8363-8370
dc.description.codenCEUJE
dc.identifier.isiut000293838300020
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