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Regioselective and Stereospecific Copper-Catalyzed Aminoboration of Styrenes with Bis(pinacolato)diboron and O‑Benzoyl‑N,N‑dialkylhydroxylamines

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journal contribution
posted on 03.04.2013, 00:00 authored by Naoki Matsuda, Koji Hirano, Tetsuya Satoh, Masahiro Miura
A Cu-catalyzed regioselective and stereospecific aminoboration of styrenes with bis­(pinacolato)­diboron and O-benzoyl-N,N-dialkylhydroxylamines that delivers the corresponding β-aminoalkylboranes in good yields has been developed. The Cu catalysis enables introduction of both amine and boron moieties to C–C double bonds simultaneously in a syn fashion. Moreover, the use of a chiral biphosphine ligand, (S,S)-Me-Duphos, provides a catalytic enantioselective route to optically active β-aminoalkylboranes.