Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives

An isothiourea-catalysed enantioselective synthesis of novel tetrahydroindolizine derivatives is reported through a one-pot tandem sequential process. The application of 2-(pyrrol-1-yl)acetic acid in combination with either a trifluoromethyl enone or an α-keto-β,γ-unsaturated ester in an enantiosele...

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Autores principales: Zhang, Shuyue, Greenhalgh, Mark D., Slawin, Alexandra M. Z., Smith, Andrew D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8152628/
https://www.ncbi.nlm.nih.gov/pubmed/34122857
http://dx.doi.org/10.1039/d0sc00432d
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author Zhang, Shuyue
Greenhalgh, Mark D.
Slawin, Alexandra M. Z.
Smith, Andrew D.
author_facet Zhang, Shuyue
Greenhalgh, Mark D.
Slawin, Alexandra M. Z.
Smith, Andrew D.
author_sort Zhang, Shuyue
collection PubMed
description An isothiourea-catalysed enantioselective synthesis of novel tetrahydroindolizine derivatives is reported through a one-pot tandem sequential process. The application of 2-(pyrrol-1-yl)acetic acid in combination with either a trifluoromethyl enone or an α-keto-β,γ-unsaturated ester in an enantioselective Michael addition–lactonisation process, followed by in situ ring-opening and cyclisation, led to a range of 24 tetrahydroindolizine derivatives containing three stereocentres in up to >95 : 5 dr and >99 : 1 er.
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spelling pubmed-81526282021-06-11 Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives Zhang, Shuyue Greenhalgh, Mark D. Slawin, Alexandra M. Z. Smith, Andrew D. Chem Sci Chemistry An isothiourea-catalysed enantioselective synthesis of novel tetrahydroindolizine derivatives is reported through a one-pot tandem sequential process. The application of 2-(pyrrol-1-yl)acetic acid in combination with either a trifluoromethyl enone or an α-keto-β,γ-unsaturated ester in an enantioselective Michael addition–lactonisation process, followed by in situ ring-opening and cyclisation, led to a range of 24 tetrahydroindolizine derivatives containing three stereocentres in up to >95 : 5 dr and >99 : 1 er. The Royal Society of Chemistry 2020-03-12 /pmc/articles/PMC8152628/ /pubmed/34122857 http://dx.doi.org/10.1039/d0sc00432d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Zhang, Shuyue
Greenhalgh, Mark D.
Slawin, Alexandra M. Z.
Smith, Andrew D.
Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives
title Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives
title_full Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives
title_fullStr Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives
title_full_unstemmed Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives
title_short Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives
title_sort tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8152628/
https://www.ncbi.nlm.nih.gov/pubmed/34122857
http://dx.doi.org/10.1039/d0sc00432d
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AT slawinalexandramz tandemsequentialcatalyticenantioselectivesynthesisofhighlyfunctionalisedtetrahydroindolizinederivatives
AT smithandrewd tandemsequentialcatalyticenantioselectivesynthesisofhighlyfunctionalisedtetrahydroindolizinederivatives

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