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Cobalt‐Catalyzed Aminocarbonylation of Alkyl Tosylates: Stereospecific Synthesis of Amides
Author(s) -
Sargent Brendon T.,
Alexanian Erik J.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201905173
Subject(s) - stereospecificity , electrophile , alkyl , chemoselectivity , amide , catalysis , chemistry , cobalt , aryl , combinatorial chemistry , organic chemistry
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.