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Simple catalytic mechanism for the direct coupling of ?-carbonyls with functionalized amines: a one-step synthesis of Plavix.

ABSTRACT: The direct ?-amination of ketones, esters, and aldehydes has been accomplished via copper catalysis. In the presence of catalytic copper(II) bromide, a diverse range of carbonyl and amine substrates undergo fragment coupling to produce synthetically useful ?-amino-substituted motifs. The transformation is proposed to proceed via a catalytically generated ?-bromo carbonyl species; nucleophilic displacement of the bromide by the amine then delivers the ?-amino carbonyl adduct while the catalyst is reconstituted. The practical value of this transformation is highlighted through one-step syntheses of two high-profile pharmaceutical agents, Plavix and amfepramone.

SUBMITTER: Evans RW

PROVIDER: S-EPMC3934301 | biostudies-other | 2013 Oct

REPOSITORIES: biostudies-other

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Simple catalytic mechanism for the direct coupling of α-carbonyls with functionalized amines: a one-step synthesis of Plavix.

Evans Ryan W RW Zbieg Jason R JR Zhu Shaolin S Li Wei W MacMillan David W C DW

Journal of the American Chemical Society 20131016 43

The direct α-amination of ketones, esters, and aldehydes has been accomplished via copper catalysis. In the presence of catalytic copper(II) bromide, a diverse range of carbonyl and amine substrates undergo fragment coupling to produce synthetically useful α-amino-substituted motifs. The transformation is proposed to proceed via a catalytically generated α-bromo carbonyl species; nucleophilic displacement of the bromide by the amine then delivers the α-amino carbonyl adduct while the catalyst is ...[more]

PMID: 24107144

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