The Influence of Microwave Irradiation on Lipase-Catalyzed Kinetic Resolution of Racemic Secondary Alcohols

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dc.contributor.author Bachu, P en
dc.contributor.author Gibson, J en
dc.contributor.author Sperry, Jonathan en
dc.contributor.author Brimble, Margaret en
dc.date.accessioned 2011-09-21T23:22:14Z en
dc.date.issued 2007 en
dc.identifier.citation TETRAHEDRON-ASYMMETR 18(13):1618-1624 17 Jul 2007 en
dc.identifier.issn 0957-4166 en
dc.identifier.uri http://hdl.handle.net/2292/8246 en
dc.description.abstract The influence of microwave irradiation on the Novozyme 435® (Candida antarctica lipase) catalyzed kinetic resolution of secondary alcohols with different functional groups was studied in comparison to the use of conventional heating at 60 °C. p-Chlorophenyl acetate was used as an acyl donor and toluene as the solvent. (±)-1-Phenyl-1-propanol 1, (±)-1-(4-bromophenyl)-propan-1-ol 3, (±)-1-phenylbut-3-en-1-ol 5 and (±)-3-bromo-2-(2-hydroxypropyl)-1,4-dimethoxynaphthalene 7 were successfully resolved into their (S)-alcohols and (R)-esters, respectively, in good enantiomeric excess. Resolution of (±)-ethyl-5-(4-methoxybenyloxy)-3-hydroxypentanoate 9 afforded its (R)-alcohol and (S)-ester using this method. In addition, microwave-assisted lipase transesterification of meso-symmetric diol 11 effected desymmetrization to ester 12 with high enantiomeric excess. In all cases studied, the conversion value for the microwave-assisted lipase kinetic resolution of secondary alcohols was higher than that obtained using conventional heating. en
dc.language EN en
dc.publisher Elsevier Ltd. en
dc.relation.ispartofseries Tetrahedron-Asymmetry en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0957-4166/ en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject ENANTIOSELECTIVE TOTAL-SYNTHESIS en
dc.subject ORGANIC-SYNTHESIS en
dc.subject IONIC LIQUIDS en
dc.subject ENHANCED ENANTIOSELECTIVITY en
dc.subject ENZYMATIC RESOLUTION en
dc.subject SYNTHETIC ROUTE en
dc.subject TRANSESTERIFICATION en
dc.subject BIOCATALYSIS en
dc.subject INHIBITOR en
dc.subject CONSTRUCTION en
dc.title The Influence of Microwave Irradiation on Lipase-Catalyzed Kinetic Resolution of Racemic Secondary Alcohols en
dc.type Journal Article en
dc.identifier.doi 10.1016/j.tetasy.2007.06.035 en
pubs.issue 13 en
pubs.begin-page 1618 en
pubs.volume 18 en
dc.rights.holder Copyright: 2007 Elsevier Ltd. en
pubs.end-page 1624 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 74023 en
pubs.org-id Science en
pubs.org-id Chemistry en
pubs.org-id Science Research en
pubs.org-id Maurice Wilkins Centre (2010-2014) en
pubs.record-created-at-source-date 2010-09-01 en


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