Catalytic Asymmetric Diamination of Styrenes

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 ox...

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Veröffentlicht in:Journal of the American Chemical Society 2017-03, Vol.139 (12), p.4354-4357
Hauptverfasser: Muñiz, Kilian, Barreiro, Laura, Romero, R. Martín, Martínez, Claudio
Format: Artikel
Sprache:eng
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Zusammenfassung: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%.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b01443