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

Author(s)
Niljianskul, Nootaree; Zhu, Shaolin; Buchwald, Stephen Leffler
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Abstract
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.
Date issued
2014-12
URI
http://hdl.handle.net/1721.1/99658
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Angewandte Chemie International Edition
Publisher
Wiley Blackwell
Citation
Niljianskul, Nootaree, Shaolin Zhu, and Stephen L. Buchwald. “Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes.” Angew. Chem. Int. Ed. 54, no. 5 (December 4, 2014): 1638–1641.
Version: Author's final manuscript
ISSN
14337851
1521-3773
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