An Enamide‐Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans

A novel method for the highly stereoselective synthesis of tetrahydropyrans is reported. This domino reaction is based on a twofold addition of enamides to aldehydes followed by a subsequent cyclization and furnishes fully substituted tetrahydropyrans in high yields. Three new σ‐bonds and five conti...

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Detalles Bibliográficos
Autores principales: Kramer, Philipp, Grimmer, Jennifer, Bolte, Michael, Manolikakes, Georg
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/PMC6772187/
https://www.ncbi.nlm.nih.gov/pubmed/31298800
http://dx.doi.org/10.1002/anie.201907565
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author Kramer, Philipp
Grimmer, Jennifer
Bolte, Michael
Manolikakes, Georg
author_facet Kramer, Philipp
Grimmer, Jennifer
Bolte, Michael
Manolikakes, Georg
author_sort Kramer, Philipp
collection PubMed
description A novel method for the highly stereoselective synthesis of tetrahydropyrans is reported. This domino reaction is based on a twofold addition of enamides to aldehydes followed by a subsequent cyclization and furnishes fully substituted tetrahydropyrans in high yields. Three new σ‐bonds and five continuous stereogenic centers are formed in this one‐pot process with a remarkable degree of diastereoselectivity. In most cases, the formation of only one out of 16 possible diastereomers is observed. Two different stereoisomers can be accessed in a controlled fashion starting either from an E‐ or a Z‐configured enamide.
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spelling pubmed-67721872019-10-07 An Enamide‐Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans Kramer, Philipp Grimmer, Jennifer Bolte, Michael Manolikakes, Georg Angew Chem Int Ed Engl Communications A novel method for the highly stereoselective synthesis of tetrahydropyrans is reported. This domino reaction is based on a twofold addition of enamides to aldehydes followed by a subsequent cyclization and furnishes fully substituted tetrahydropyrans in high yields. Three new σ‐bonds and five continuous stereogenic centers are formed in this one‐pot process with a remarkable degree of diastereoselectivity. In most cases, the formation of only one out of 16 possible diastereomers is observed. Two different stereoisomers can be accessed in a controlled fashion starting either from an E‐ or a Z‐configured enamide. John Wiley and Sons Inc. 2019-08-07 2019-09-09 /pmc/articles/PMC6772187/ /pubmed/31298800 http://dx.doi.org/10.1002/anie.201907565 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
Kramer, Philipp
Grimmer, Jennifer
Bolte, Michael
Manolikakes, Georg
An Enamide‐Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans
title An Enamide‐Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans
title_full An Enamide‐Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans
title_fullStr An Enamide‐Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans
title_full_unstemmed An Enamide‐Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans
title_short An Enamide‐Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans
title_sort enamide‐based domino reaction for a highly stereoselective synthesis of tetrahydropyrans
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6772187/
https://www.ncbi.nlm.nih.gov/pubmed/31298800
http://dx.doi.org/10.1002/anie.201907565
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