Niljianskul Nootaree, Zhu Shaolin, Buchwald Stephen L
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139 (USA).
Angew Chem Int Ed Engl. 2015 Jan 26;54(5):1638-41. doi: 10.1002/anie.201410326. Epub 2014 Dec 4.
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.
报道了通过铜催化乙烯基硅烷的高度对映选择性和区域选择性氢胺化反应合成α-氨基硅烷。该体系使用Cu-DTBM-SEGPHOS作为催化剂,二乙氧基甲基硅烷作为化学计量的还原剂,以及O-苯甲酰基羟胺作为亲电氮源。这种氢胺化反应与不同取代的乙烯基硅烷兼容,从而能够合成氨基酸类似物和其他有价值的手性有机硅化合物。