Dynamic kinetic resolution of 2-methyl-2-nitrocyclohexanol: Combining the intramolecular nitroaldol (Henry) reaction & lipase catalysed resolution

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dc.contributor.authorFoley, Aoife M.
dc.contributor.authorGavin, Declan P.
dc.contributor.authorDeasy, Rebecca E.
dc.contributor.authorMilner, Sinéad E.
dc.contributor.authorMoody, Thomas S.
dc.contributor.authorEccles, Kevin S.
dc.contributor.authorLawrence, Simon E.
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderIrish Research Council for Science, Engineering and Technologyen
dc.contributor.funderEli Lilly and Companyen
dc.contributor.funderPfizeren
dc.contributor.funderScience Foundation Irelanden
dc.date.accessioned2018-02-09T12:49:21Z
dc.date.available2018-02-09T12:49:21Z
dc.date.issued2018-02-02
dc.date.updated2018-02-07T11:39:40Z
dc.description.abstractEfforts to combine the intramolecular nitroaldol reaction with lipase-catalysed resolution of the resulting nitroaldol adduct in a one-pot dynamic kinetic resolution (DKR) are described. Significant challenges were encountered in the combination of the two systems. trans-2-Methyl-2-nitrocyclohexyl acetate (±)-3b was isolated in excellent enantiopurity (>98% ee) via a sequential DKR sequence where the lipase-mediated resolution and base-mediated interconversion of 2-methyl-2-nitrocyclohexanol 2 were effected alternately, demonstrating the feasibility of this approach initially. Further work showed, for the first time, evidence that a DKR-type system is possible for 2. Reaction engineering allowed the design of a sequential one-pot reaction system which furnished the products with excellent enantioselectivity, and good diastereoselectivity.en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationFoley, A. M., Gavin, D. P.; Deasy, R. E., Milner, S. E., Moody, T. S., Eccles, K. S., Lawrence, S. E. and Maguire, A. R. (2018) 'Dynamic kinetic resolution of 2-methyl-2-nitrocyclohexanol: Combining the intramolecular nitroaldol (Henry) reaction & lipase catalysed resolution', Tetrahedron, 74(13), pp. 1435-1443. doi:10.1016/j.tet.2018.01.055en
dc.identifier.doi10.1016/j.tet.2018.01.055
dc.identifier.endpage1443
dc.identifier.issn0040-4020
dc.identifier.issued13
dc.identifier.journaltitleTetrahedronen
dc.identifier.startpage1435
dc.identifier.urihttps://hdl.handle.net/10468/5435
dc.identifier.volume74
dc.language.isoenen
dc.publisherElsevier B.V.en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
dc.rights© 2018, Elsevier B.V. All rights reserved. This manuscript version is made available under the CC-BY-NC-ND 4.0 license.en
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/en
dc.subjectBiocatalysisen
dc.subjectKinetic resolutionen
dc.subjectHenry reactionen
dc.subjectDynamic kinetic resolutionen
dc.subjectLipasesen
dc.titleDynamic kinetic resolution of 2-methyl-2-nitrocyclohexanol: Combining the intramolecular nitroaldol (Henry) reaction & lipase catalysed resolutionen
dc.typeArticle (peer-reviewed)en
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