Enantioselective synthesis of α-aminosilanes by copper-catalyzed hydroamination of vinylsilanes.

Angew Chem Int Ed Engl

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139 (USA).

Published: January 2015

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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4384418PMC
http://dx.doi.org/10.1002/anie.201410326DOI Listing

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