Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 5, Pages 1638-1641Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201410326
Keywords
asymmetric synthesis; copper; hydroamination; silicon
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Funding
- National Institutes of Health [GM58160]
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The synthesis of alpha-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.
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