Chiral β-nitroalcohols are important building blocks in organic chemistry. The synthetic approach Chiralthat is β-nitroalcoholsbased on the enzyme-mediated are important building reduction blocks of in α-nitroketones organic chemistry. has Thebeensyntheticscarcely approachconsidered.thatIn thisis basedwork,onthetheuseenzyme-mediatedof commercial alcoholreductiondehydrogenasesof α-nitroketones(ADHs)hasfor beenthe reductionscarcely considered.of aromatic andIn thisaliphaticwork, thenitroketonesuse of commercialis investigated.alcoholHighdehydrogenasesconversions (ADHs)and enantioselectivitiesfor the reductioncanof aromaticbe achievedandwithaliphatictwo specificnitroketonesADHs,isaffordinginvestigated.eitherHighthe conversions(S) or (R)-enantiomerand enantioselectivitiesof the correspondingcan be achievednitroalcohols.with twoThe specificreactionADHs,conditionsaffordingare carefullyeither thetuned(S) orto(R)-enantiomerpreserve the stabilityof the correspondingof the reduced nitroalcohols.product, and toTheavoidreactionthe hydrolyticconditionsdegradationare carefullyof thetunedstartingto preservesubstrate.theThestabilityfurtherofmanipulationthe reduced product,ofof thethe enantioenrichedenantioenrichedand to avoid thenitroalcoholsnitroalcoholshydrolytic degradationintointo Boc-protectedBoc-protectedof the startingamminoalcoholsamminoalcoholssubstrate.isisThealsoalsofurtherdescribed.described.manipulation.

Biocatalytic approach to chiral beta-nitroalcohols by enantioselective alcohol dehydrogenase-mediated reduction of alpha-nitroketones

TENTORI, FRANCESCA;E. Brenna;COLOMBO, DANILO;M. Crotti;F. G. Gatti;GHEZZI, MARIA CHIARA;
2018

Abstract

Chiral β-nitroalcohols are important building blocks in organic chemistry. The synthetic approach Chiralthat is β-nitroalcoholsbased on the enzyme-mediated are important building reduction blocks of in α-nitroketones organic chemistry. has Thebeensyntheticscarcely approachconsidered.thatIn thisis basedwork,onthetheuseenzyme-mediatedof commercial alcoholreductiondehydrogenasesof α-nitroketones(ADHs)hasfor beenthe reductionscarcely considered.of aromatic andIn thisaliphaticwork, thenitroketonesuse of commercialis investigated.alcoholHighdehydrogenasesconversions (ADHs)and enantioselectivitiesfor the reductioncanof aromaticbe achievedandwithaliphatictwo specificnitroketonesADHs,isaffordinginvestigated.eitherHighthe conversions(S) or (R)-enantiomerand enantioselectivitiesof the correspondingcan be achievednitroalcohols.with twoThe specificreactionADHs,conditionsaffordingare carefullyeither thetuned(S) orto(R)-enantiomerpreserve the stabilityof the correspondingof the reduced nitroalcohols.product, and toTheavoidreactionthe hydrolyticconditionsdegradationare carefullyof thetunedstartingto preservesubstrate.theThestabilityfurtherofmanipulationthe reduced product,ofof thethe enantioenrichedenantioenrichedand to avoid thenitroalcoholsnitroalcoholshydrolytic degradationintointo Boc-protectedBoc-protectedof the startingamminoalcoholsamminoalcoholssubstrate.isisThealsoalsofurtherdescribed.described.manipulation.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11311/1082345
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