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Counterion-Enhanced Pd/Enamine Catalysis: Direct Asymmetric α-Allylation of Aldehydes with Allylic Alcohols by Chiral Amines and Achiral or Racemic Phosphoric Acids

[Image: see text] We report a straightforward and efficient Pd/enamine catalytic procedure for the direct asymmetric α-allylation of branched aldehydes. The use of simple chiral amines and easily prepared achiral or racemic phosphoric acids, together with a suitable Pd-source resulted in a highly ac...

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Autores principales: Pálvölgyi, Ádám Márk, Smith, Jakob, Schnürch, Michael, Bica-Schröder, Katharina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7783732/
https://www.ncbi.nlm.nih.gov/pubmed/33320681
http://dx.doi.org/10.1021/acs.joc.0c02385
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author Pálvölgyi, Ádám Márk
Smith, Jakob
Schnürch, Michael
Bica-Schröder, Katharina
author_facet Pálvölgyi, Ádám Márk
Smith, Jakob
Schnürch, Michael
Bica-Schröder, Katharina
author_sort Pálvölgyi, Ádám Márk
collection PubMed
description [Image: see text] We report a straightforward and efficient Pd/enamine catalytic procedure for the direct asymmetric α-allylation of branched aldehydes. The use of simple chiral amines and easily prepared achiral or racemic phosphoric acids, together with a suitable Pd-source resulted in a highly active and enantioselective catalyst system for the allylation of various α-branched aldehydes with different allylic alcohols. The reported procedure could provide an easy access to both product antipodes. Furthermore, two possible orthogonal derivatizations of the enantioenriched aldehydes were performed without any decrease in enantioselectivity.
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spelling pubmed-77837322021-01-06 Counterion-Enhanced Pd/Enamine Catalysis: Direct Asymmetric α-Allylation of Aldehydes with Allylic Alcohols by Chiral Amines and Achiral or Racemic Phosphoric Acids Pálvölgyi, Ádám Márk Smith, Jakob Schnürch, Michael Bica-Schröder, Katharina J Org Chem [Image: see text] We report a straightforward and efficient Pd/enamine catalytic procedure for the direct asymmetric α-allylation of branched aldehydes. The use of simple chiral amines and easily prepared achiral or racemic phosphoric acids, together with a suitable Pd-source resulted in a highly active and enantioselective catalyst system for the allylation of various α-branched aldehydes with different allylic alcohols. The reported procedure could provide an easy access to both product antipodes. Furthermore, two possible orthogonal derivatizations of the enantioenriched aldehydes were performed without any decrease in enantioselectivity. American Chemical Society 2020-12-15 2021-01-01 /pmc/articles/PMC7783732/ /pubmed/33320681 http://dx.doi.org/10.1021/acs.joc.0c02385 Text en © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Pálvölgyi, Ádám Márk
Smith, Jakob
Schnürch, Michael
Bica-Schröder, Katharina
Counterion-Enhanced Pd/Enamine Catalysis: Direct Asymmetric α-Allylation of Aldehydes with Allylic Alcohols by Chiral Amines and Achiral or Racemic Phosphoric Acids
title Counterion-Enhanced Pd/Enamine Catalysis: Direct Asymmetric α-Allylation of Aldehydes with Allylic Alcohols by Chiral Amines and Achiral or Racemic Phosphoric Acids
title_full Counterion-Enhanced Pd/Enamine Catalysis: Direct Asymmetric α-Allylation of Aldehydes with Allylic Alcohols by Chiral Amines and Achiral or Racemic Phosphoric Acids
title_fullStr Counterion-Enhanced Pd/Enamine Catalysis: Direct Asymmetric α-Allylation of Aldehydes with Allylic Alcohols by Chiral Amines and Achiral or Racemic Phosphoric Acids
title_full_unstemmed Counterion-Enhanced Pd/Enamine Catalysis: Direct Asymmetric α-Allylation of Aldehydes with Allylic Alcohols by Chiral Amines and Achiral or Racemic Phosphoric Acids
title_short Counterion-Enhanced Pd/Enamine Catalysis: Direct Asymmetric α-Allylation of Aldehydes with Allylic Alcohols by Chiral Amines and Achiral or Racemic Phosphoric Acids
title_sort counterion-enhanced pd/enamine catalysis: direct asymmetric α-allylation of aldehydes with allylic alcohols by chiral amines and achiral or racemic phosphoric acids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7783732/
https://www.ncbi.nlm.nih.gov/pubmed/33320681
http://dx.doi.org/10.1021/acs.joc.0c02385
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