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A Nucleophilic Strategy for Enantioselective Intermolecular ?-Amination: Access to Enantioenriched ?-Arylamino Ketones.

ABSTRACT: The enantioselective addition of anilines to azoalkenes was accomplished through the use of a chiral phosphoric acid catalyst. The resulting ?-arylamino hydrazones were obtained in good yields and excellent enantioselectivities and provide access to enantioenriched ?-arylamino ketones. A serendipitous kinetic resolution of racemic ?-arylamino hydrazones is also described.

SUBMITTER: Miles DH

PROVIDER: S-EPMC5152760 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones.

Miles Dillon H DH Guasch Joan J Toste F Dean FD

Journal of the American Chemical Society 20150612 24

The enantioselective addition of anilines to azoalkenes was accomplished through the use of a chiral phosphoric acid catalyst. The resulting α-arylamino hydrazones were obtained in good yields and excellent enantioselectivities and provide access to enantioenriched α-arylamino ketones. A serendipitous kinetic resolution of racemic α-arylamino hydrazones is also described. ...[more]

PMID: 26066512

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