title: Synthesis of β-Boryl-α-Aminosilanes by Copper-Catalyzed Aminoboration of Vinylsilanes.
abstract: A copper-catalyzed regioselective and stereospecific aminoboration of vinylsilanes with bis(pinacolato)diboron (pinB-Bpin) and hydroxylamines has been developed. In the presence of a CuCl/MeO-dppbz catalyst, the boryl group and amino group are incorporated at the β position and α position, respectively, and the corresponding β-boryl-α-aminosilanes are obtained with good diastereoselectivity. The boryl group is a good latent functional group, and subsequent manipulations provide a variety of β-functionalized α-aminosilanes of great potential in medicinal chemistry. Additionally, preliminary application to asymmetric catalysis is also described.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan.
authors.forename: Kodai
authors.initials: K
authors.lastname: Kato
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan. k_hirano@chem.eng.osaka-u.ac.jp.
authors.forename: Koji
authors.initials: K
authors.lastname: Hirano
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan. miura@chem.eng.osaka-u.ac.jp.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Miura
keywords: boron; copper; electrophilic amination; synthetic methods; α-aminosilanes