Cobalt-Catalyzed Aminocarbonylation of Alkyl Tosylates: Stereospecific Synthesis of Amides.
alkyl tosylates
aminocarbonylation
cobalt
homogenous catalysis
synthetic methods
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
08 07 2019
08 07 2019
Historique:
received:
25
04
2019
pubmed:
16
5
2019
medline:
15
9
2020
entrez:
16
5
2019
Statut:
ppublish
Résumé
Metal-catalyzed aminocarbonylation is a standard approach for installing amide functionality in chemical synthesis. Despite broad application of this transformation using aryl or vinyl electrophiles, there are few examples involving unactivated aliphatic substrates. Furthermore, there are no stereocontrolled aminocarbonylations of alkyl electrophiles known. Herein, we report a stereospecific aminocarbonylation of unactivated alkyl tosylates for the synthesis of enantioenriched amides. This cobalt-catalyzed transformation uses a remarkably broad range of amines and proceeds with excellent stereospecificity and chemoselectivity.
Identifiants
pubmed: 31087438
doi: 10.1002/anie.201905173
pmc: PMC7070179
mid: NIHMS1029827
doi:
Substances chimiques
Amides
0
Cobalt
3G0H8C9362
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Langues
eng
Sous-ensembles de citation
IM
Pagination
9533-9536Subventions
Organisme : NIGMS NIH HHS
ID : R01 GM107204
Pays : United States
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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