Enantiomerically pure thiahelicenes displaying a terminal phosphole unit and a stereogenic phosphorus center have been prepared by oxidative photocyclization of a diaryl-olefin precursor. Starting from one of these phosphathiahelicene oxides, the corresponding trivalent phosphine-Au(I) complex is obtained with complete diastereoselectivity. It affords a new, excellent precatalyst for the enantioselective cycloisomerization of N-tethered enynes (up to 96 % ee).
Phosphathiahelicenes : synthesis and uses in enantioselective gold catalysis / P. Aillard, A. Voituriez, D. Dova, S. Cauteruccio, E. Licandro, A. Marinetti. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 20:39(2014 Sep 22), pp. 12373-12376. [10.1002/chem.201402822]
Phosphathiahelicenes : synthesis and uses in enantioselective gold catalysis
D. Dova;S. Cauteruccio;E. Licandro
;
2014
Abstract
Enantiomerically pure thiahelicenes displaying a terminal phosphole unit and a stereogenic phosphorus center have been prepared by oxidative photocyclization of a diaryl-olefin precursor. Starting from one of these phosphathiahelicene oxides, the corresponding trivalent phosphine-Au(I) complex is obtained with complete diastereoselectivity. It affords a new, excellent precatalyst for the enantioselective cycloisomerization of N-tethered enynes (up to 96 % ee).
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