Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of δ4-2,7-Disubstituted Oxepenes

A direct iron(III)-catalyzed Prins-Peterson reaction involving α-substituted γ-triphenylsilyl bis-homoallylic alcohols and aldehydes is described. Thus, cis--2,7-disubstituted oxepenes were synthesized in a diastereoselective reaction using sustainable catalytic conditions (3-5 mol %). This highly p...

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Autores: Cruz, Daniel A., Sinka, Victoria, Martín, Víctor S., Padrón, Juan I.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/179831
Acceso en línea:http://hdl.handle.net/10261/179831
Access Level:acceso abierto
Palabra clave:Oxepenes
Synthesis
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spelling Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of δ4-2,7-Disubstituted OxepenesCruz, Daniel A.Sinka, VictoriaMartín, Víctor S.Padrón, Juan I.OxepenesSynthesisA direct iron(III)-catalyzed Prins-Peterson reaction involving α-substituted γ-triphenylsilyl bis-homoallylic alcohols and aldehydes is described. Thus, cis--2,7-disubstituted oxepenes were synthesized in a diastereoselective reaction using sustainable catalytic conditions (3-5 mol %). This highly productive process is the result of a cascade of three chemical events with the concomitant formation of a C-O bond, a C-C bond, and a endocyclic double bond, through a Prins cyclization followed by a Peterson-type elimination. This tandem reaction is chemoselective vs the classical Prins cyclization.This research was supported by the Spanish MINECO and ACIISI (Gobierno de Canarias), cofinanced by the European Regional Development Fund (ERDF) (CTQ2014-56362-C2-1-P and ProID2017010118). D.A.C. thanks the Spanish MINECO for an F.P.I. fellowship. V.S. thanks Cajasiete-ULL for a predoctoral contract.Peer ReviewedAmerican Chemical SocietyAgencia Canaria de Investigación, Innovación y Sociedad de la InformaciónMinisterio de Economía, Industria y Competitividad (España)European CommissionConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2019201920182019info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/179831reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-56362-C2-1-P; https://doi.org/10.1021/acs.joc.8b01978Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1798312026-05-22T06:33:51Z
dc.title.none.fl_str_mv Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of δ4-2,7-Disubstituted Oxepenes
title Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of δ4-2,7-Disubstituted Oxepenes
spellingShingle Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of δ4-2,7-Disubstituted Oxepenes
Cruz, Daniel A.
Oxepenes
Synthesis
title_short Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of δ4-2,7-Disubstituted Oxepenes
title_full Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of δ4-2,7-Disubstituted Oxepenes
title_fullStr Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of δ4-2,7-Disubstituted Oxepenes
title_full_unstemmed Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of δ4-2,7-Disubstituted Oxepenes
title_sort Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of δ4-2,7-Disubstituted Oxepenes
dc.creator.none.fl_str_mv Cruz, Daniel A.
Sinka, Victoria
Martín, Víctor S.
Padrón, Juan I.
author Cruz, Daniel A.
author_facet Cruz, Daniel A.
Sinka, Victoria
Martín, Víctor S.
Padrón, Juan I.
author_role author
author2 Sinka, Victoria
Martín, Víctor S.
Padrón, Juan I.
author2_role author
author
author
dc.contributor.none.fl_str_mv Agencia Canaria de Investigación, Innovación y Sociedad de la Información
Ministerio de Economía, Industria y Competitividad (España)
European Commission
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Oxepenes
Synthesis
topic Oxepenes
Synthesis
description A direct iron(III)-catalyzed Prins-Peterson reaction involving α-substituted γ-triphenylsilyl bis-homoallylic alcohols and aldehydes is described. Thus, cis--2,7-disubstituted oxepenes were synthesized in a diastereoselective reaction using sustainable catalytic conditions (3-5 mol %). This highly productive process is the result of a cascade of three chemical events with the concomitant formation of a C-O bond, a C-C bond, and a endocyclic double bond, through a Prins cyclization followed by a Peterson-type elimination. This tandem reaction is chemoselective vs the classical Prins cyclization.
publishDate 2018
dc.date.none.fl_str_mv 2018
2019
2019
2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/179831
url http://hdl.handle.net/10261/179831
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-56362-C2-1-P;
https://doi.org/10.1021/acs.joc.8b01978
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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