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

ABSTRACT: The synthesis of ?-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.

SUBMITTER: Niljianskul N

PROVIDER: S-EPMC4384418 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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

Niljianskul Nootaree N Zhu Shaolin S Buchwald Stephen L SL

Angewandte Chemie (International ed. in English) 20141204 5

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. ...[more]

PMID: 25475991

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