American Chemical Society
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Catalytic Asymmetric Diamination of Styrenes

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posted on 2017-03-09, 00:00 authored by Kilian Muñiz, Laura Barreiro, R. Martín Romero, Claudio Martínez
An enantioselective catalytic vicinal diamination of styrenes is reported, which proceeds under entirely intermolecular reaction control. It relies on a chirally modified aryliodine­(I) catalyst and proceeds within an iodine­(I/III) manifold with conventional 3-chloroperbenzoic acid as a terminal oxidant. An environmentally benign solvent combination not only adds to the attractiveness of the process but also slows down the rate of the undesired background reaction. A total of 30 examples are presented, which consistently provide high enantiomeric excesses in the range 91–98%.