First enantioselective catalyst for the rearrangement of allylic imidates to allylic amides

M Calter, TK Hollis, LE Overman, J Ziller…

Index: Calter, Michael; Hollis, T. Keith; Overman, Larry E.; Ziller, Joseph; Zipp, G. Greg Journal of Organic Chemistry, 1997 , vol. 62, # 5 p. 1449 - 1456

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Citation Number: 156

Abstract

A series of Pd (II) complexes containing chiral diamine ligands were investigated as asymmetric catalysts for the rearrangement of allylic imidates to allyl amides. The best catalysts were cations obtained by dechlorination of dichloro [(S)-2-(isoindolinylmethyl)-N- methylpyrrolidine] palladium (II)(17) with silver salts in CH2Cl2. Catalyst 18 was studied thoroughly and shown by 1H NMR and X-ray crystallography analysis to be a C 1 ...