Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes

The synthesis of α-aminosilanes by a highly enantio- and regioselective copper-catalyzed hydroamination of vinylsilanes is reported. The system employs Cu-DTBM-SEGPHOS as the catalyst, diethoxymethylsilane as the stoichiometric reductant, and O-benzoylhydroxylamines as the electrophilic nitrogen sou...

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Bibliographic Details
Main Authors: Niljianskul, Nootaree (Contributor), Zhu, Shaolin (Contributor), Buchwald, Stephen Leffler (Contributor)
Other Authors: Massachusetts Institute of Technology. Department of Chemistry (Contributor)
Format: Article
Language:English
Published: Wiley Blackwell, 2015-11-02T19:07:55Z.
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Online Access:Get fulltext
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100 1 0 |a Niljianskul, Nootaree  |e author 
100 1 0 |a Massachusetts Institute of Technology. Department of Chemistry  |e contributor 
100 1 0 |a Niljianskul, Nootaree  |e contributor 
100 1 0 |a Zhu, Shaolin  |e contributor 
100 1 0 |a Buchwald, Stephen Leffler  |e contributor 
700 1 0 |a Zhu, Shaolin  |e author 
700 1 0 |a Buchwald, Stephen Leffler  |e author 
245 0 0 |a Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes 
260 |b Wiley Blackwell,   |c 2015-11-02T19:07:55Z. 
856 |z Get fulltext  |u http://hdl.handle.net/1721.1/99658 
520 |a The synthesis of α-aminosilanes by a highly enantio- and regioselective copper-catalyzed hydroamination of vinylsilanes is reported. The system employs Cu-DTBM-SEGPHOS as the catalyst, diethoxymethylsilane as the stoichiometric reductant, and O-benzoylhydroxylamines as the electrophilic nitrogen source. This hydroamination reaction is compatible with differentially substituted vinylsilanes, thus providing access to amino acid mimics and other valuable chiral organosilicon compounds. 
520 |a National Institutes of Health (U.S.) (Award GM58160) 
546 |a en_US 
655 7 |a Article 
773 |t Angewandte Chemie International Edition