Enzymatic Kinetic Resolution of Tertiary Benzyl Bicyclic Alcohols: Studies of the Reaction Conditions for a More Efficient Protocol

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MetadadosDescriçãoIdioma
Autor(es): dc.contributorUniversidade Estadual Paulista (UNESP)-
Autor(es): dc.creatorde Almeida, Laiza A.-
Autor(es): dc.creatorNeto, Laerte Ganéo-
Autor(es): dc.creatorMilagre, Cintia D.F.-
Autor(es): dc.creatorMilagre, Humberto M.S.-
Data de aceite: dc.date.accessioned2025-08-21T19:17:15Z-
Data de disponibilização: dc.date.available2025-08-21T19:17:15Z-
Data de envio: dc.date.issued2025-04-29-
Data de envio: dc.date.issued2023-12-31-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.21577/0103-5053.20240033-
Fonte completa do material: dc.identifierhttps://hdl.handle.net/11449/300215-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/300215-
Descrição: dc.descriptionThe reactivity and steric hindrance of optically active tertiary alcohols limit the development of more direct enantioselective methodologies for their synthesis, such as kinetic resolution (KR). In this work, we optimized the reaction conditions of an enzymatic KR of two tertiary benzyl bicyclic alcohols using readily available reagents and biocatalyst. Studies were conducted with 1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol and 1-methyl-2,3-dihydro-1H-inden-1-ol as substrates and commercial lipase A from Candida antarctica (CAL-A) as biocatalyst for the enantioselective transesterification of these racemic tertiary alcohols. After varying the reaction parameters, such as acyl donor, solvent, and enzyme/substrate ratio, the (R)-esters were obtained with high conversions (44-45%) and excellent enantiomeric excess (96-99%) in only 4-5 h, to our knowledge being the best result for KR of the evaluated tertiary alcohols in terms of reaction rate, conversion, and enantioselectivity reported so far.-
Descrição: dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)-
Descrição: dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)-
Descrição: dc.descriptionInstituto de Química Universidade Estadual Paulista “Júlio de Mesquita Filho” (UNESP), SP-
Descrição: dc.descriptionInstituto de Química Universidade Estadual Paulista “Júlio de Mesquita Filho” (UNESP), SP-
Descrição: dc.descriptionCAPES: 001-
Descrição: dc.descriptionFAPESP: 2019/15230-8-
Idioma: dc.languageen-
Relação: dc.relationJournal of the Brazilian Chemical Society-
???dc.source???: dc.sourceScopus-
Palavras-chave: dc.subjectenantioselective transesterification-
Palavras-chave: dc.subjectkinetic resolution-
Palavras-chave: dc.subjectlipase-
Palavras-chave: dc.subjecttertiary alcohol-
Título: dc.titleEnzymatic Kinetic Resolution of Tertiary Benzyl Bicyclic Alcohols: Studies of the Reaction Conditions for a More Efficient Protocol-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional - Unesp

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