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. 2013 Oct 23;135(42):15746-9.
doi: 10.1021/ja4092819. Epub 2013 Oct 15.

Enantio- and regioselective CuH-catalyzed hydroamination of alkenes

Shaolin Zhu  1 , Nootaree Niljianskul, Stephen L Buchwald
Affiliations

Enantio- and regioselective CuH-catalyzed hydroamination of alkenes

Shaolin Zhu et al. J Am Chem Soc. .

Abstract

A highly enantio- and regioselective copper-catalyzed hydroamination reaction of alkenes has been developed using diethoxymethylsilane and esters of hydroxylamines. The process tolerates a wide variety of substituted styrenes, including trans-, cis-, and β,β-disubstituted styrenes, to yield α-branched amines. In addition, aliphatic alkenes coupled to generate exclusively the anti-Markovnikov hydroamination products.

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Figures

Figure 1
Figure 1
Proposed catalytic cycle for CuH catalyzed hydroamination of alkenes
Scheme 1
Scheme 1
Anti-Markovnikov Hydroamination of Aliphatic Alkene
Scheme 2
Scheme 2
Large-scale Hydroamination Reaction of β-substituted Styrene
See this image and copyright information in PMC

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