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Título

Novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents

AutorAbad, José Luis; Soldevila, Carles; Camps Díez, Francisco; Clapés Saborit, Pere
Palabras claveChemoenzymatic methodology
Secondary alcohols
Enzymatic resolution
Sex pheromone biosynthesis
Fecha de publicación5-jun-2003
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 68(13): 5351-5356 (2003)
ResumenA 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.
Descripción6 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/jo0341113
Versión del editorhttp://dx.doi.org/10.1021/jo0341113
URIhttp://hdl.handle.net/10261/20227
DOI10.1021/jo0341113
ISSN0022-3263 (Print)
1520-6904 (Online)
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