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dc.contributor.authorAbad, José Luis-
dc.contributor.authorSoldevila, Carles-
dc.contributor.authorCamps Díez, Francisco-
dc.contributor.authorClapés Saborit, Pere-
dc.date.accessioned2010-01-21T09:38:43Z-
dc.date.available2010-01-21T09:38:43Z-
dc.date.issued2003-06-05-
dc.identifier.citationJournal of Organic Chemistry 68(13): 5351-5356 (2003)en_US
dc.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/10261/20227-
dc.description6 pages, 2 figures, 1 scheme, 2 tables.-- PMID: 12816498 [PubMed].-- Printed version published Jun 27, 2003.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo0341113en_US
dc.description.abstractA novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents is described. The key step is the kinetic lipase-catalyzed resolution of racemic mixtures of substituted propargylic alcohols. The efficiency of this new approach was tested in the preparation of the corresponding enantiomers of 1,11-hexadecandiol derivatives ((R)-5 and (S)-5). Two strategies were tested. In the first one, the racemic intermediate 1-octyn-3-ol (1) was resolved enzymatically and then elongated with 1-bromo-9,11-dioxadodecane. Alternatively, the racemic 1 can be elongated to the corresponding racemic 17,19-dioxa-7-eicosyn-6-ol (3) first and then resolved biocatalytically. Twelve commercially available lipases were screened for the kinetic resolution of these intermediates. Among them, Candida antarctica lipase (CAL-B) and Humicola lanuginosa lipase (HLL) were the best biocatalysts for the resolution of 1 (S enantiomer 90% ee, E = 35), and 3 (R enantiomer 90% ee, E = 34), respectively.en_US
dc.description.sponsorshipCICYT and FEDER (AGL2001-0585) and Generalitat de Catalunya (2001SGR 00342).en_US
dc.format.extent22195 bytes-
dc.format.mimetypeapplication/pdf-
dc.language.isoengen_US
dc.publisherAmerican Chemical Societyen_US
dc.rightsclosedAccessen_US
dc.subjectChemoenzymatic methodologyen_US
dc.subjectSecondary alcoholsen_US
dc.subjectEnzymatic resolutionen_US
dc.subjectSex pheromone biosynthesisen_US
dc.titleNovel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituentsen_US
dc.typeartículoen_US
dc.identifier.doi10.1021/jo0341113-
dc.description.peerreviewedPeer revieweden_US
dc.relation.publisherversionhttp://dx.doi.org/10.1021/jo0341113en_US
dc.identifier.e-issn1520-6904-
dc.type.coarhttp://purl.org/coar/resource_type/c_6501es_ES
item.openairetypeartículo-
item.cerifentitytypePublications-
item.languageiso639-1en-
item.grantfulltextnone-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.fulltextNo Fulltext-
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