A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives

A regio‐ and chemoselective preparation of bicyclic alkoxyoxazolium salts from amide derivatives of proline and pipecolic acid by electrophilic amide activation is reported. Mechanistic NMR experiments suggest an unusual role for the base and highlight the effect of substitution pattern of the subst...

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Detalles Bibliográficos
Autores principales: Spinozzi, Eleonora, Bauer, Adriano, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6771909/
https://www.ncbi.nlm.nih.gov/pubmed/31598092
http://dx.doi.org/10.1002/ejoc.201900985
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author Spinozzi, Eleonora
Bauer, Adriano
Maulide, Nuno
author_facet Spinozzi, Eleonora
Bauer, Adriano
Maulide, Nuno
author_sort Spinozzi, Eleonora
collection PubMed
description A regio‐ and chemoselective preparation of bicyclic alkoxyoxazolium salts from amide derivatives of proline and pipecolic acid by electrophilic amide activation is reported. Mechanistic NMR experiments suggest an unusual role for the base and highlight the effect of substitution pattern of the substrates.
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spelling pubmed-67719092019-10-07 A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives Spinozzi, Eleonora Bauer, Adriano Maulide, Nuno European J Org Chem Communications A regio‐ and chemoselective preparation of bicyclic alkoxyoxazolium salts from amide derivatives of proline and pipecolic acid by electrophilic amide activation is reported. Mechanistic NMR experiments suggest an unusual role for the base and highlight the effect of substitution pattern of the substrates. John Wiley and Sons Inc. 2019-08-08 2019-09-01 /pmc/articles/PMC6771909/ /pubmed/31598092 http://dx.doi.org/10.1002/ejoc.201900985 Text en © 2019 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Spinozzi, Eleonora
Bauer, Adriano
Maulide, Nuno
A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives
title A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives
title_full A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives
title_fullStr A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives
title_full_unstemmed A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives
title_short A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives
title_sort mild synthesis of bicyclic alkoxyoxazolium salts from proline and pipecolic acid derivatives
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6771909/
https://www.ncbi.nlm.nih.gov/pubmed/31598092
http://dx.doi.org/10.1002/ejoc.201900985
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