Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches

This minireview focuses on recent advances in the synthesis of seven‐membered ring oxacycles, whether saturated, unsaturated, fused or isolated. We cover a remarkable variety of strategies and methods developed during the past two decades, based mainly on cyclizations, ring‐closing metathesis, conju...

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Detalhes bibliográficos
Autores: Sinka, Victoria, Martín, Víctor S., Cruz, Daniel A., Padrón, Juan I.
Formato: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2020
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/219040
Acesso em linha:http://hdl.handle.net/10261/219040
Access Level:acceso abierto
Palavra-chave:Oxepane
Oxepene
Seven‐membered rings
Oxepine
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spelling Synthesis of Seven Membered Oxacycles: Recent Developments and New ApproachesSinka, VictoriaMartín, Víctor S.Cruz, Daniel A.Padrón, Juan I.OxepaneOxepeneSeven‐membered ringsOxepineThis minireview focuses on recent advances in the synthesis of seven‐membered ring oxacycles, whether saturated, unsaturated, fused or isolated. We cover a remarkable variety of strategies and methods developed during the past two decades, based mainly on cyclizations, ring‐closing metathesis, conjugate additions, and ring expansions. The cyclizations can be generated directly or triggered through an oxocarbenium ion, carbocation or iminium‐type species. Also discussed are ring‐closing metatheses and conjugate additions, in which the precursor has the functionalities and correct stereochemistry of the final seven‐membered ring oxacycle. Finally, examples of ring expansions are described, predominantly involving cyclopropanes and epoxides. These cases include reactions governed by the intermediate species and others, where the precursor holds the stereochemical information for the final oxacycle.This research was supported by the Ministerio de Ciencia, Innovación y Universidades (MCIU), la Agencia Estatal de Investigación (AEI), Fondo Europeo de Desarrollo Regional (FEDER) and ACIISI (Gobierno de Canarias) (PGC2018‐094503‐B–C22 and ProID2017010118). V. S. thanks the Spanish MCIU for an F.P.U. fellowship. D. A. C. thanks the Cabildo de Tenerife for a postdoctoral Agustín de Betancourt contract. The manuscript was edited by Guido Jones, also funded currently by Cabildo de Tenerife under the TFinnova Program, supported by MEDI and FDCAN.Peer reviewedWiley-VCHMinisterio de Ciencia, Innovación y Universidades (España)Gobierno de CanariasAgencia Estatal de Investigación (España)Cabildo de TenerifeConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202020202020info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/219040reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttps://doi.org/10.1002/ejoc.202000850Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2190402026-05-22T06:33:51Z
dc.title.none.fl_str_mv Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches
title Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches
spellingShingle Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches
Sinka, Victoria
Oxepane
Oxepene
Seven‐membered rings
Oxepine
title_short Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches
title_full Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches
title_fullStr Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches
title_full_unstemmed Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches
title_sort Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches
dc.creator.none.fl_str_mv Sinka, Victoria
Martín, Víctor S.
Cruz, Daniel A.
Padrón, Juan I.
author Sinka, Victoria
author_facet Sinka, Victoria
Martín, Víctor S.
Cruz, Daniel A.
Padrón, Juan I.
author_role author
author2 Martín, Víctor S.
Cruz, Daniel A.
Padrón, Juan I.
author2_role author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia, Innovación y Universidades (España)
Gobierno de Canarias
Agencia Estatal de Investigación (España)
Cabildo de Tenerife
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Oxepane
Oxepene
Seven‐membered rings
Oxepine
topic Oxepane
Oxepene
Seven‐membered rings
Oxepine
description This minireview focuses on recent advances in the synthesis of seven‐membered ring oxacycles, whether saturated, unsaturated, fused or isolated. We cover a remarkable variety of strategies and methods developed during the past two decades, based mainly on cyclizations, ring‐closing metathesis, conjugate additions, and ring expansions. The cyclizations can be generated directly or triggered through an oxocarbenium ion, carbocation or iminium‐type species. Also discussed are ring‐closing metatheses and conjugate additions, in which the precursor has the functionalities and correct stereochemistry of the final seven‐membered ring oxacycle. Finally, examples of ring expansions are described, predominantly involving cyclopropanes and epoxides. These cases include reactions governed by the intermediate species and others, where the precursor holds the stereochemical information for the final oxacycle.
publishDate 2020
dc.date.none.fl_str_mv 2020
2020
2020
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/10261/219040
url http://hdl.handle.net/10261/219040
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://doi.org/10.1002/ejoc.202000850
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
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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score 15,811543

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