4.7 Article

Enantioselective Platinum-Catalyzed Tandem Hydroarylation-Cycloisomerization of 1,6-Enynes

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 14-15, Pages 2401-2408

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800446

Keywords

asymmetric catalysis; atom economy; cycloisomerization; platinum; tandem reactions

Funding

  1. Ministere de l'Education et de la Recherche

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The platinum(II) chloride/silver hexafluoroantimonate (PtCl2/AgSbF6) catalytic system associated with atropisomeric ligand Ph-BI-NEPINE promotes a stereoselective tandem hydroarylation (Friedel-Crafts-type addition) of electron-rich aromatic and heteroaromatic derivatives to un-activated alkenes followed by a C-C bond cyclization reaction (ee up to 96%). Some evidence shows that the catalytic species responsible for the highest enantiomeric excesses might reasonably be an L3Pt2+ species, L being a monodentate ligand.

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