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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2020
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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. |
format | Online Article Text |
id | pubmed-7783732 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
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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