Synthesis of [beta]-Boryl-[alpha]-Aminosilanes by Copper-Catalyzed Aminoboration of Vinylsilanes

Synthesis of [beta]-Boryl-[alpha]-Aminosilanes by Copper-Catalyzed Aminoboration of Vinylsilanes

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 [beta] position and [alpha] position...

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Veröffentlicht in:Angewandte Chemie 2016-11, Vol.128 (46), p.14612
Hauptverfasser: Kato, Kodai, Hirano, Koji, Miura, Masahiro
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Hirano, Koji
Miura, Masahiro
description 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 [beta] position and [alpha] position, respectively, and the corresponding [beta]-boryl-[alpha]-aminosilanes are obtained with good diastereoselectivity. The boryl group is a good latent functional group, and subsequent manipulations provide a variety of [beta]-functionalized [alpha]-aminosilanes of great potential in medicinal chemistry. Additionally, preliminary application to asymmetric catalysis is also described.
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title Synthesis of [beta]-Boryl-[alpha]-Aminosilanes by Copper-Catalyzed Aminoboration of Vinylsilanes
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