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Simple Catalytic Mechanism for the Direct Coupling of α-Carbonyls with Functionalized Amines: A One-Step Synthesis of Plavix

Ryan W. Evans, Jason R. Zbieg, Shaolin Zhu, Wei Li and David W. C. MacMillan*

*Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States, Email: dmacmillprinceton.edu

R. W. Evans. J. R. Zbieg, S. Wu, W. Li, D. W. C. MacMillan, J. Am. Chem. Soc., 2013, 135, 16074-16077.

DOI: 10.1021/ja4096472 (free Supporting Information)



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Abstract

In the presence of catalytic copper(II) bromide, a direct α-amination of ketones, esters, and aldehydes takes place to produce synthetically useful α-amino-substituted motifs. The transformation is proposed to proceed via a catalytically generated α-bromo carbonyl species followed by nucleophilic displacement of the bromide by the amine, which delivers the α-amino carbonyl adduct while the catalyst is reconstituted.

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Key Words

α-amination, oxygen


ID: J48-Y2013