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Enantio- and Regioselective CuH-Catalyzed Hydroamination of Alkenes

Shaolin Zhu, Nootaree Niljianskul and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu

S. Zhu, N. Niljianskul, S. L. Buchwald, J. Am. Chem. Soc., 2013, 135, 15746-15749.

DOI: 10.1021/ja4092819 (free Supporting Information)


Abstract

A highly enantio- and regioselective copper-catalyzed hydroamination reaction of alkenes with hydroxylamine esters in the presence of diethoxymethylsilane enables the conversion of a wide variety of substituted styrenes, including trans-, cis-, and β,β-disubstituted styrenes, to yield α-branched amines. In addition, aliphatic alkenes gave exclusively the anti-Markovnikov hydroamination products.

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Key Words

benzylamines, amines, DEMS


ID: J48-Y2013