Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles...

Autores: Bisogno, Fabricio Román; Cuetos, Aníbal; Orden, Alejandro Agustin; Kurina Sanz, Marcela Beatriz; Lavandera, Iván; Gotor, Vicente
Año de publicación: 2010
Idioma: inglés
Tipo de recurso: artículo
Estado: versión publicada
Descripción: Different enantiopure terminal epoxides or bromohydrins have chemoselectively been synthesised in one-pot starting from the corresponding a-bromo ketones through alcohol dehydrogenase (ADH)-catalysed processes adding an organic cosolvent and tuning appropriately the medium pH and the temperature. Thus, at neutral pH enantiopure bromohydrins were obtained while using basic conditions (pH 9.5–10) epoxides were isolated as the main product. Furthermore, by simple selection of the biocatalyst, chemo- and stereodivergent transformations were achieved to obtain, e.g., enantiopure prolinol or piperidin-3-ol.
Fil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Cuetos, Aníbal. Universidad de Oviedo; España
Fil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Lavandera, Iván. Universidad de Oviedo; España
Fil: Gotor, Vicente. Universidad de Oviedo; España
Materia: ALCOHOL DEHYDROGENASE
BROMOHYDRYNE
EPOXIDES
MEDIUM ENGINEERING
ONE POT REACTION
PROLINOL
Nivel de accesibilidad: acceso abierto
Condiciones de uso: https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
Institución: Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador: oai:ri.conicet.gov.ar:11336/280477

Acceder

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repository_id_str	3498
network_name_str	CONICET Digital (CONICET)
spelling	Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐HeterocyclesBisogno, Fabricio RománCuetos, AníbalOrden, Alejandro AgustinKurina Sanz, Marcela BeatrizLavandera, IvánGotor, VicenteALCOHOL DEHYDROGENASEBROMOHYDRYNEEPOXIDESMEDIUM ENGINEERINGONE POT REACTIONPROLINOLhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Different enantiopure terminal epoxides or bromohydrins have chemoselectively been synthesised in one-pot starting from the corresponding a-bromo ketones through alcohol dehydrogenase (ADH)-catalysed processes adding an organic cosolvent and tuning appropriately the medium pH and the temperature. Thus, at neutral pH enantiopure bromohydrins were obtained while using basic conditions (pH 9.5–10) epoxides were isolated as the main product. Furthermore, by simple selection of the biocatalyst, chemo- and stereodivergent transformations were achieved to obtain, e.g., enantiopure prolinol or piperidin-3-ol.Fil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Cuetos, Aníbal. Universidad de Oviedo; EspañaFil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Lavandera, Iván. Universidad de Oviedo; EspañaFil: Gotor, Vicente. Universidad de Oviedo; EspañaWiley VCH Verlag2010-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/280477Bisogno, Fabricio Román; Cuetos, Aníbal; Orden, Alejandro Agustin; Kurina Sanz, Marcela Beatriz; Lavandera, Iván; et al.; Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles; Wiley VCH Verlag; Advanced Synthesis & Catalysis (print); 352; 10; 6-2010; 1657-16611615-4150CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/adsc.201000353/fullinfo:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201000353info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-02-26T10:35:24Zoai:ri.conicet.gov.ar:11336/280477instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982026-02-26 10:35:24.816CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv	Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles
title	Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles
spellingShingle	Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles Bisogno, Fabricio Román ALCOHOL DEHYDROGENASE BROMOHYDRYNE EPOXIDES MEDIUM ENGINEERING ONE POT REACTION PROLINOL
title_short	Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles
title_full	Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles
title_fullStr	Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles
title_full_unstemmed	Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles
title_sort	Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles
dc.creator.none.fl_str_mv	Bisogno, Fabricio Román Cuetos, Aníbal Orden, Alejandro Agustin Kurina Sanz, Marcela Beatriz Lavandera, Iván Gotor, Vicente
author	Bisogno, Fabricio Román
author_facet	Bisogno, Fabricio Román Cuetos, Aníbal Orden, Alejandro Agustin Kurina Sanz, Marcela Beatriz Lavandera, Iván Gotor, Vicente
author_role	author
author2	Cuetos, Aníbal Orden, Alejandro Agustin Kurina Sanz, Marcela Beatriz Lavandera, Iván Gotor, Vicente
author2_role	author author author author author
dc.subject.none.fl_str_mv	ALCOHOL DEHYDROGENASE BROMOHYDRYNE EPOXIDES MEDIUM ENGINEERING ONE POT REACTION PROLINOL
topic	ALCOHOL DEHYDROGENASE BROMOHYDRYNE EPOXIDES MEDIUM ENGINEERING ONE POT REACTION PROLINOL
purl_subject.fl_str_mv	https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv	Different enantiopure terminal epoxides or bromohydrins have chemoselectively been synthesised in one-pot starting from the corresponding a-bromo ketones through alcohol dehydrogenase (ADH)-catalysed processes adding an organic cosolvent and tuning appropriately the medium pH and the temperature. Thus, at neutral pH enantiopure bromohydrins were obtained while using basic conditions (pH 9.5–10) epoxides were isolated as the main product. Furthermore, by simple selection of the biocatalyst, chemo- and stereodivergent transformations were achieved to obtain, e.g., enantiopure prolinol or piperidin-3-ol. Fil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Cuetos, Aníbal. Universidad de Oviedo; España Fil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina Fil: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina Fil: Lavandera, Iván. Universidad de Oviedo; España Fil: Gotor, Vicente. Universidad de Oviedo; España
description	Different enantiopure terminal epoxides or bromohydrins have chemoselectively been synthesised in one-pot starting from the corresponding a-bromo ketones through alcohol dehydrogenase (ADH)-catalysed processes adding an organic cosolvent and tuning appropriately the medium pH and the temperature. Thus, at neutral pH enantiopure bromohydrins were obtained while using basic conditions (pH 9.5–10) epoxides were isolated as the main product. Furthermore, by simple selection of the biocatalyst, chemo- and stereodivergent transformations were achieved to obtain, e.g., enantiopure prolinol or piperidin-3-ol.
publishDate	2010
dc.date.none.fl_str_mv	2010-06
dc.type.none.fl_str_mv	info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo
format	article
status_str	publishedVersion
dc.identifier.none.fl_str_mv	http://hdl.handle.net/11336/280477 Bisogno, Fabricio Román; Cuetos, Aníbal; Orden, Alejandro Agustin; Kurina Sanz, Marcela Beatriz; Lavandera, Iván; et al.; Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles; Wiley VCH Verlag; Advanced Synthesis & Catalysis (print); 352; 10; 6-2010; 1657-1661 1615-4150 CONICET Digital CONICET
url	http://hdl.handle.net/11336/280477
identifier_str_mv	Bisogno, Fabricio Román; Cuetos, Aníbal; Orden, Alejandro Agustin; Kurina Sanz, Marcela Beatriz; Lavandera, Iván; et al.; Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles; Wiley VCH Verlag; Advanced Synthesis & Catalysis (print); 352; 10; 6-2010; 1657-1661 1615-4150 CONICET Digital CONICET
dc.language.none.fl_str_mv	eng
language	eng
dc.relation.none.fl_str_mv	info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/adsc.201000353/full info:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201000353
dc.rights.none.fl_str_mv	info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv	openAccess
rights_invalid_str_mv	https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv	application/pdf application/pdf application/pdf application/pdf
dc.publisher.none.fl_str_mv	Wiley VCH Verlag
publisher.none.fl_str_mv	Wiley VCH Verlag
dc.source.none.fl_str_mv	reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str	CONICET Digital (CONICET)
collection	CONICET Digital (CONICET)
instname_str	Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv	CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv	dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score	12.665996

Chemo‐ and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One‐Pot Biocatalysed Reactions: Access to Enantiopure Five‐ and Six‐Membered N‐Heterocycles...

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