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Chemo‐ and Stereoselective Synthesis of Fluorinated Amino Alcohols through One‐pot Reactions using Alcohol Dehydrogenases and Amine Transaminases

dc.contributor.authorGonzález Martínez, Daniel 
dc.contributor.authorGotor Santamaría, Vicente Miguel 
dc.contributor.authorGotor Fernández, Vicente 
dc.date.accessioned2020-12-11T07:28:29Z
dc.date.available2020-12-11T07:28:29Z
dc.date.issued2020
dc.identifier.citationAdvanced Synthesis & Catalysis, 362(23), p. 5398-5410 (2020); doi:10.1002/adsc.202000798
dc.identifier.issn1615-4150
dc.identifier.urihttp://hdl.handle.net/10651/57193
dc.description.abstractA series of amino alcohols have been prepared in a chemo-, diastereo- and enantioselective fashion starting from the corresponding (het)aryl diketones, avoiding tedious chemical protection and deprotection steps. Different alcohol dehydrogenases have been able to selectively reduce the more reactive trifluoroacetyl groups under optimized conditions, while amine transaminases catalyzed the biotransamination of the less hindered acetyl groups. Based on the different reactivity of the acetyl and trifluoroacetyl groups, the design of sequential and concurrent cascades was investigated. The proper selection of the enzymes permits the synthesis of amino alcohol stereoisomers in high to excellent yields (86->99% conversion) and remarkable stereocontrol (up to >99% de and >99% ee) using an aqueous medium and mild reaction conditions.spa
dc.description.sponsorshipFinancial support of this work by the Spanish Ministry of Economy and Competitiveness (MINECO, CTQ2016-75752-R project) and Asturian Regional Government (FC-GRUPINIDI/2018/000181) are gratefully acknowledged. D.G.-M. thanks also Asturian Regional Government for a predoctoral fellowship.spa
dc.format.extentp. 5398-5410spa
dc.language.isoengspa
dc.relation.ispartofAdvanced Synthesis & Catalysis, 362spa
dc.rights© 2020 Wiley‐VCH GmbH
dc.rightsCC Reconocimiento - No Comercial - Sin Obra Derivada 4.0 Internacional
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.titleChemo‐ and Stereoselective Synthesis of Fluorinated Amino Alcohols through One‐pot Reactions using Alcohol Dehydrogenases and Amine Transaminasesspa
dc.typejournal articlespa
dc.identifier.doi10.1002/adsc.202000798
dc.relation.projectIDMINECO/CTQ2016-75752-Rspa
dc.relation.projectIDFC-GRUPINIDI/2018/000181spa
dc.relation.publisherversionhttps://doi.org/10.1002/adsc.202000798spa
dc.rights.accessRightsopen accessspa
dc.type.hasVersionAM


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