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Enantioselective Synthesis of α‐Aminosilanes by Copper‐Catalyzed Hydroamination of Vinylsilanes
Author(s) -
Niljianskul Nootaree,
Zhu Shaolin,
Buchwald Stephen L.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201410326
Subject(s) - hydroamination , organosilicon , chemistry , catalysis , regioselectivity , enantioselective synthesis , copper , electrophile , organic chemistry , combinatorial chemistry
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.