Biocatalytic approach to chiral β-nitroalcohols by enantioselective alcohol dehydrogenase-mediated reduction of α-nitroketones

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.