Salt-Free Iridium-Catalyzed Asymmetric Allylic Aminations with N,N-Diacylamines and ortho-Nosylamide as Ammonia Equivalents


  • This work was supported by the Deutsche Forschungsgemeinschaft (SFB 623) and the Fonds der Chemischen Industrie. We thank Prof. K. Ditrich (BASF AG) for enantiomerically pure 1-arylethylamines and Q. Stang for helpful information.


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New variants of the iridium-catalyzed allylic substitution allow N-protected and non-protected chiral allylamines to be prepared with high enantio- and regioselectivity. The allylamines are used as nucleophiles in highly diastereoselective, catalyst-controlled allylic aminations. The products are transformed into N-non-protected 2,5-disubstituted 3,4-dehydropyrrolidines by ring-closing metathesis (RCM; see scheme).