Pd‐Catalyzed Allylation of Imines to Access α‐CF(3)‐Substituted α‐Amino Acid Derivatives

We herein report a high yielding protocol for the direct α‐allylation of easily accessible trifluoropyruvate‐derived imines using Pd‐catalysis. The reaction gives access to a variety of different α‐allylated‐α‐CF(3)‐amino acids in a straightforward manner, starting from commercially available triflu...

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Detalles Bibliográficos
Autores principales: Winter, Michael, Kim, Hyunwoo, Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6887540/
https://www.ncbi.nlm.nih.gov/pubmed/31798337
http://dx.doi.org/10.1002/ejoc.201901272
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author Winter, Michael
Kim, Hyunwoo
Waser, Mario
author_facet Winter, Michael
Kim, Hyunwoo
Waser, Mario
author_sort Winter, Michael
collection PubMed
description We herein report a high yielding protocol for the direct α‐allylation of easily accessible trifluoropyruvate‐derived imines using Pd‐catalysis. The reaction gives access to a variety of different α‐allylated‐α‐CF(3)‐amino acids in a straightforward manner, starting from commercially available trifluoropyruvate. We also provide a proof‐of‐concept for an enantioselective protocol (up to er = 75:25) by using chiral phosphane ligands.
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spelling pubmed-68875402019-12-03 Pd‐Catalyzed Allylation of Imines to Access α‐CF(3)‐Substituted α‐Amino Acid Derivatives Winter, Michael Kim, Hyunwoo Waser, Mario European J Org Chem Full Papers We herein report a high yielding protocol for the direct α‐allylation of easily accessible trifluoropyruvate‐derived imines using Pd‐catalysis. The reaction gives access to a variety of different α‐allylated‐α‐CF(3)‐amino acids in a straightforward manner, starting from commercially available trifluoropyruvate. We also provide a proof‐of‐concept for an enantioselective protocol (up to er = 75:25) by using chiral phosphane ligands. John Wiley and Sons Inc. 2019-11-06 2019-11-14 /pmc/articles/PMC6887540/ /pubmed/31798337 http://dx.doi.org/10.1002/ejoc.201901272 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 Full Papers
Winter, Michael
Kim, Hyunwoo
Waser, Mario
Pd‐Catalyzed Allylation of Imines to Access α‐CF(3)‐Substituted α‐Amino Acid Derivatives
title Pd‐Catalyzed Allylation of Imines to Access α‐CF(3)‐Substituted α‐Amino Acid Derivatives
title_full Pd‐Catalyzed Allylation of Imines to Access α‐CF(3)‐Substituted α‐Amino Acid Derivatives
title_fullStr Pd‐Catalyzed Allylation of Imines to Access α‐CF(3)‐Substituted α‐Amino Acid Derivatives
title_full_unstemmed Pd‐Catalyzed Allylation of Imines to Access α‐CF(3)‐Substituted α‐Amino Acid Derivatives
title_short Pd‐Catalyzed Allylation of Imines to Access α‐CF(3)‐Substituted α‐Amino Acid Derivatives
title_sort pd‐catalyzed allylation of imines to access α‐cf(3)‐substituted α‐amino acid derivatives
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6887540/
https://www.ncbi.nlm.nih.gov/pubmed/31798337
http://dx.doi.org/10.1002/ejoc.201901272
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AT kimhyunwoo pdcatalyzedallylationofiminestoaccessacf3substitutedaaminoacidderivatives
AT wasermario pdcatalyzedallylationofiminestoaccessacf3substitutedaaminoacidderivatives

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