Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals

A direct and asymmetric syn-aldol reaction of N-acyl-1,3-oxazinane-2-thiones with dialkyl acetals from aromatic acetals in the presence of 2-5 mol % [DTBM-SEGPHOS]NiCl2, TMSOTf, and lutidine has been developed. It has been established that the oxazinanethione heterocycle, used for the first time as...

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Authors: Mellado Hidalgo, Miguel, Romero Cavagnaro, Elias A., Nageswaran, Sajanthanaa, Puddu, Sabrina, Kennington, Stuart C. D., Costa i Arnau, Anna M., Romea, Pedro, Urpí Tubella, Fèlix, Aullón López, Gabriel, Font Bardia, Ma. Mercedes
Format: article
Status:Versión aceptada para publicación
Publication Date:2023
Country:España
Institution:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repository:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/196206
Online Access:https://hdl.handle.net/2445/196206
Access Level:Open access
Keyword:Aldehids
Estructura molecular
Aldehydes
Molecular structure
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spelling Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetalsMellado Hidalgo, MiguelRomero Cavagnaro, Elias A.Nageswaran, SajanthanaaPuddu, SabrinaKennington, Stuart C. D.Costa i Arnau, Anna M.Romea, PedroUrpí Tubella, FèlixAullón López, GabrielFont Bardia, Ma. MercedesAldehidsEstructura molecularAldehydesMolecular structureA direct and asymmetric syn-aldol reaction of N-acyl-1,3-oxazinane-2-thiones with dialkyl acetals from aromatic acetals in the presence of 2-5 mol % [DTBM-SEGPHOS]NiCl2, TMSOTf, and lutidine has been developed. It has been established that the oxazinanethione heterocycle, used for the first time as a scaffold in asymmetric carbon-carbon bond-forming reactions, can be smoothly removed to give access to a variety of enantiomerically pure compounds with high synthetic value.American Chemical Society2023202420232023info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion5 p.application/pdfapplication/pdfhttps://hdl.handle.net/2445/196206Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésVersió postprint del document publicat a: https://doi.org/10.1021/acs.orglett.2c04254Organic Letters, 2023, vol. 23, num. 4, p. 659-664https://doi.org/10.1021/acs.orglett.2c04254(c) American Chemical Society , 2023info:eu-repo/semantics/openAccessoai:recercat.cat:2445/1962062026-05-29T05:05:01Z
dc.title.none.fl_str_mv Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals
title Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals
spellingShingle Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals
Mellado Hidalgo, Miguel
Aldehids
Estructura molecular
Aldehydes
Molecular structure
title_short Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals
title_full Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals
title_fullStr Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals
title_full_unstemmed Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals
title_sort Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals
dc.creator.none.fl_str_mv Mellado Hidalgo, Miguel
Romero Cavagnaro, Elias A.
Nageswaran, Sajanthanaa
Puddu, Sabrina
Kennington, Stuart C. D.
Costa i Arnau, Anna M.
Romea, Pedro
Urpí Tubella, Fèlix
Aullón López, Gabriel
Font Bardia, Ma. Mercedes
author Mellado Hidalgo, Miguel
author_facet Mellado Hidalgo, Miguel
Romero Cavagnaro, Elias A.
Nageswaran, Sajanthanaa
Puddu, Sabrina
Kennington, Stuart C. D.
Costa i Arnau, Anna M.
Romea, Pedro
Urpí Tubella, Fèlix
Aullón López, Gabriel
Font Bardia, Ma. Mercedes
author_role author
author2 Romero Cavagnaro, Elias A.
Nageswaran, Sajanthanaa
Puddu, Sabrina
Kennington, Stuart C. D.
Costa i Arnau, Anna M.
Romea, Pedro
Urpí Tubella, Fèlix
Aullón López, Gabriel
Font Bardia, Ma. Mercedes
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Aldehids
Estructura molecular
Aldehydes
Molecular structure
topic Aldehids
Estructura molecular
Aldehydes
Molecular structure
description A direct and asymmetric syn-aldol reaction of N-acyl-1,3-oxazinane-2-thiones with dialkyl acetals from aromatic acetals in the presence of 2-5 mol % [DTBM-SEGPHOS]NiCl2, TMSOTf, and lutidine has been developed. It has been established that the oxazinanethione heterocycle, used for the first time as a scaffold in asymmetric carbon-carbon bond-forming reactions, can be smoothly removed to give access to a variety of enantiomerically pure compounds with high synthetic value.
publishDate 2023
dc.date.none.fl_str_mv 2023
2023
2023
2024
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 https://hdl.handle.net/2445/196206
url https://hdl.handle.net/2445/196206
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1021/acs.orglett.2c04254
Organic Letters, 2023, vol. 23, num. 4, p. 659-664
https://doi.org/10.1021/acs.orglett.2c04254
dc.rights.none.fl_str_mv (c) American Chemical Society , 2023
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) American Chemical Society , 2023
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 5 p.
application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
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
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,81155

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