Synlett, Inhaltsverzeichnis LETTER © Georg Thieme Verlag Stuttgart · New York Novel Catalysts for the Overman Rearrangement Ieva Jaunzemea, Aigars Jirgensons*b a Faculty of Material Science and Applied Chemistry, Riga Technical University, Riga 1048, Latviab Latvian Institute of Organic Synthesis, Riga 1006, LatviaFax: +371(7)541408; e-Mail: aigars@osi.lv; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract PtCl2, PtCl4, AuCl, and AuCl3 were found to be efficient catalysts for the Overman rearrangement of O-allyltrichloroacetimidates to N-allyltrichloroacetamides. Key words amines - amides - rearrangement - catalysis - Lewis acids Volltext Referenzen References 1a Overman LE. J. Am. Chem. Soc. 1974, 96: 597 1b Overman LE. J. Am. Chem. Soc. 1976, 98: 290 1c Overman LE. Acc. Chem. Res. 1980, 13: 218 1d Anderson CE. Overman LE. J. Am. Chem. Soc. 2003, 125: 12412 1e Kirsch S. Overman EL. Watson MP. J. Org. Chem. 2004, 69: 8101 2 Johannsen M. Jorgensen KA. Chem. Rev. 1998, 98: 1689 3a Metz P. Shoop A. Tetrahedron 1992, 48: 1071 3b Overman LE. Angew. Chem., Int. Ed. Engl. 1984, 23: 579 3c Singh OV. Han H. Org. Lett. 2004, 6: 3067 4a Jamieson AG. Sutherland A. Org. Biomol. Chem. 2005, 3: 737 4b Ovaa H. Codee JDC. Lastdrager B. Overkleeft HS. van der Marel GA. van Boom JH. Tetrahedron Lett. 1999, 40: 5063 5a Doherty AM. Kornberg BE. Reily MD. J. Org. Chem. 1993, 58: 795 5b Gonda J. Helland A.-C. Ernst B. Bellu D. Synthesis 1993, 729 6a Schenck TG. Bosnich B. J. Am. Chem. Soc. 1985, 107: 2058 6b Overman LE. Zipp GG. J. Org. Chem. 1997, 62: 2288 7 Introduction of an amino group at a tertiary carbon has been achieved using Hg(II)-catalyzed Overman rearrangement.1a In our hands, imidate 1d with PdCl2(PhCN)2 also gave a very low yield of amide 2d due to competitive elimination of trichloroacetamide (4). 8a Sabat M. Johnson CR. Org. Lett. 2000, 2: 1089 8b For related reactions see: Overman LE. Remarchuk TP. J. Am. Chem. Soc. 2002, 124: 12 9 Duffus JH. Pure Appl. Chem. 2002, 74: 793
