Cascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines

[Image: see text] A metal-free protocol for the synthesis of substituted 1,6-dihydropyridines with quaternary stereogenic centers via a cascade aza-Wittig/6π-electrocyclization process has been developed. The high functional group compatibility and broad scope of this method were demonstrated by usi...

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Autores principales: Polychronidou, Vasiliki, Krupp, Anna, Strohmann, Carsten, Antonchick, Andrey P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8397428/
https://www.ncbi.nlm.nih.gov/pubmed/34291925
http://dx.doi.org/10.1021/acs.orglett.1c02099
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author Polychronidou, Vasiliki
Krupp, Anna
Strohmann, Carsten
Antonchick, Andrey P.
author_facet Polychronidou, Vasiliki
Krupp, Anna
Strohmann, Carsten
Antonchick, Andrey P.
author_sort Polychronidou, Vasiliki
collection PubMed
description [Image: see text] A metal-free protocol for the synthesis of substituted 1,6-dihydropyridines with quaternary stereogenic centers via a cascade aza-Wittig/6π-electrocyclization process has been developed. The high functional group compatibility and broad scope of this method were demonstrated by using a wide range of easily available vinyliminophosphoranes and ketones, with yields up to 97%. A modification of the obtained products allowed for an increase in complexity and chemical diversity. Finally, attempts for asymmetric synthesis of 1,6-dihydropyridines are demonstrated.
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spelling pubmed-83974282021-08-31 Cascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines Polychronidou, Vasiliki Krupp, Anna Strohmann, Carsten Antonchick, Andrey P. Org Lett [Image: see text] A metal-free protocol for the synthesis of substituted 1,6-dihydropyridines with quaternary stereogenic centers via a cascade aza-Wittig/6π-electrocyclization process has been developed. The high functional group compatibility and broad scope of this method were demonstrated by using a wide range of easily available vinyliminophosphoranes and ketones, with yields up to 97%. A modification of the obtained products allowed for an increase in complexity and chemical diversity. Finally, attempts for asymmetric synthesis of 1,6-dihydropyridines are demonstrated. American Chemical Society 2021-07-22 2021-08-06 /pmc/articles/PMC8397428/ /pubmed/34291925 http://dx.doi.org/10.1021/acs.orglett.1c02099 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Polychronidou, Vasiliki
Krupp, Anna
Strohmann, Carsten
Antonchick, Andrey P.
Cascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines
title Cascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines
title_full Cascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines
title_fullStr Cascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines
title_full_unstemmed Cascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines
title_short Cascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines
title_sort cascade aza-wittig/6π-electrocyclization in the synthesis of 1,6-dihydropyridines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8397428/
https://www.ncbi.nlm.nih.gov/pubmed/34291925
http://dx.doi.org/10.1021/acs.orglett.1c02099
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