Asymmetric Synthesis of Homoallylic Alcohols featuring Vicinal Tetrasubstituted Carbon Centers via Dual Pd/Photoredox Catalysis

Dual palladium/photoredox-catalysis provides an effective method for the asymmetric synthesis of vicinal α,β-tri/tetra- or α,β-tetra-substituted homoallylic alcohols. Regio- and enantioselective decarboxylative allylic alkylation of vinyl cyclic carbonates is reported using Hantzsch type esters as r...

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Autores: Xue, Sijing, Limburg, Bart, Ghorai, Debasish, Benet-Buchholz, Jordi, Kleij, Arjan W.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2021
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/521280
Acceso en línea:http://hdl.handle.net/2072/521280
https://doi.org/10.1021/acs.orglett.1c01380
Access Level:acceso abierto
Palabra clave:54
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spelling Asymmetric Synthesis of Homoallylic Alcohols featuring Vicinal Tetrasubstituted Carbon Centers via Dual Pd/Photoredox CatalysisXue, SijingLimburg, BartGhorai, DebasishBenet-Buchholz, JordiKleij, Arjan W.54Dual palladium/photoredox-catalysis provides an effective method for the asymmetric synthesis of vicinal α,β-tri/tetra- or α,β-tetra-substituted homoallylic alcohols. Regio- and enantioselective decarboxylative allylic alkylation of vinyl cyclic carbonates is reported using Hantzsch type esters as radical precursors. The developed methodology combines the use of versatile and accessible reagents and can be operated under mild reaction conditions giving the target molecules in appreciable to good yields, high branch-selectivity and appreciable enantiomeric ratios of up to 94:6. This protocol marks a rare example of the use of prochiral electrophiles for the creation of vicinal congested carbon centers.2021info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion4447 p.application/vnd.openxmlformats-officedocument.wordprocessingml.documenthttp://hdl.handle.net/2072/521280https://doi.org/10.1021/acs.orglett.1c01380RECERCAT (Dipòsit de la Recerca de Catalunya)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésMINECO (CTQ2017-88920-P)AGAUR (2017-SGR-232)Severo Ochoa Excellence Accreditation 2020–2023 CEX2019-000925-SPHOTOCARBOX-889754AGAUR (2018-BP-00243)You have selected the Attribution-NonCommercial-NoDerivatives 4.0 International License. This license is permanently located at http://creativecommons.org/licenses/by-nc-nd/4.0/.info:eu-repo/semantics/openAccessoai:recercat.cat:2072/5212802026-05-29T05:05:01Z
dc.title.none.fl_str_mv Asymmetric Synthesis of Homoallylic Alcohols featuring Vicinal Tetrasubstituted Carbon Centers via Dual Pd/Photoredox Catalysis
title Asymmetric Synthesis of Homoallylic Alcohols featuring Vicinal Tetrasubstituted Carbon Centers via Dual Pd/Photoredox Catalysis
spellingShingle Asymmetric Synthesis of Homoallylic Alcohols featuring Vicinal Tetrasubstituted Carbon Centers via Dual Pd/Photoredox Catalysis
Xue, Sijing
54
title_short Asymmetric Synthesis of Homoallylic Alcohols featuring Vicinal Tetrasubstituted Carbon Centers via Dual Pd/Photoredox Catalysis
title_full Asymmetric Synthesis of Homoallylic Alcohols featuring Vicinal Tetrasubstituted Carbon Centers via Dual Pd/Photoredox Catalysis
title_fullStr Asymmetric Synthesis of Homoallylic Alcohols featuring Vicinal Tetrasubstituted Carbon Centers via Dual Pd/Photoredox Catalysis
title_full_unstemmed Asymmetric Synthesis of Homoallylic Alcohols featuring Vicinal Tetrasubstituted Carbon Centers via Dual Pd/Photoredox Catalysis
title_sort Asymmetric Synthesis of Homoallylic Alcohols featuring Vicinal Tetrasubstituted Carbon Centers via Dual Pd/Photoredox Catalysis
dc.creator.none.fl_str_mv Xue, Sijing
Limburg, Bart
Ghorai, Debasish
Benet-Buchholz, Jordi
Kleij, Arjan W.
author Xue, Sijing
author_facet Xue, Sijing
Limburg, Bart
Ghorai, Debasish
Benet-Buchholz, Jordi
Kleij, Arjan W.
author_role author
author2 Limburg, Bart
Ghorai, Debasish
Benet-Buchholz, Jordi
Kleij, Arjan W.
author2_role author
author
author
author
dc.subject.none.fl_str_mv 54
topic 54
description Dual palladium/photoredox-catalysis provides an effective method for the asymmetric synthesis of vicinal α,β-tri/tetra- or α,β-tetra-substituted homoallylic alcohols. Regio- and enantioselective decarboxylative allylic alkylation of vinyl cyclic carbonates is reported using Hantzsch type esters as radical precursors. The developed methodology combines the use of versatile and accessible reagents and can be operated under mild reaction conditions giving the target molecules in appreciable to good yields, high branch-selectivity and appreciable enantiomeric ratios of up to 94:6. This protocol marks a rare example of the use of prochiral electrophiles for the creation of vicinal congested carbon centers.
publishDate 2021
dc.date.none.fl_str_mv 2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/2072/521280
https://doi.org/10.1021/acs.orglett.1c01380
url http://hdl.handle.net/2072/521280
https://doi.org/10.1021/acs.orglett.1c01380
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv MINECO (CTQ2017-88920-P)
AGAUR (2017-SGR-232)
Severo Ochoa Excellence Accreditation 2020–2023 CEX2019-000925-S
PHOTOCARBOX-889754
AGAUR (2018-BP-00243)
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 4447 p.
application/vnd.openxmlformats-officedocument.wordprocessingml.document
dc.source.none.fl_str_mv RECERCAT (Dipòsit de la Recerca de Catalunya)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
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repository.mail.fl_str_mv
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