Synthesis of Polyfunctional Unsaturated Amines by the Addition of Functionalized Organomagnesium Reagents to Unsaturated Imminium Ions

Abstract

The reaction of propargylic and allylic aminals with tri­fluoromethanesulfonic anhydride at low temperature produces imminium salts, which react in the presence of N-methylpyrrolidinone (NMP) with functionalized arylmagnesium compounds, providing polyfunctional propargylic and allylic amines in satisfactory yields.

Key words

functionalized organomagnesium reagents - imminium salts - propargylic amines - allylic amines - aminals

References

• 1 Boudier A. Bromm LO. Lotz M. Knochel P. Angew. Chem. Int. Ed.  2000,  39:  4415 
• 2 Knochel P. Millot N. Rodriguez AL. Tucher CA. Organic Reacions   58:  Overman LE. Wiley & Sons Ltd.; New York: 2001.  p.417 
• 3a Boymond L. Rottländer M. Cahiez G. Knochel P. Angew. Chem.Int. Ed.  1998,  37:  1701 
• 3b Rottländer M. Boymond L. Bérillon L. Leprêtre A. Varchi G. Avolio S. Laaziri H. Queguiner G. Ricci A. Cahiez G. Knochel P. Chem.-Eur. J.  2000,  6:  767 
• 3c Varchi G. Jensen AE. Dohle W. Ricci A. Cahiez G. Knochel P. Synlett  2001,  477 
• 3d Sapountzis I. Knochel P. Angew. Chem. Int. Ed.  2002,  41:  1610 
• 4a Huffman MA. Yasuda N. DeCamp AE. Grabowski EJJ. J. Org. Chem.  1995,  60:  1590 
• 4b Koninski M. Okhuma H. Tsnuno T. Oki T. Van Duyne GD. Chardy JJ. J. Am. Chem. Soc.  1990,  112:  3715 
• 5 Weingarten H. Tetrahedron  1968,  24:  2767 
• 6 Bredereck H. Simchen G. Horn P. Chem. Ber.  1970,  103:  210 
• 7a Sekiya M. Sakai H. Chem. Pharm. Bull.  1969,  17:  32 
• 7b Betschart C. Schmidt B. Seebach D. Helv. Chim. Acta  1988,  71:  1999 
• 8 Millot N. Piazza C. Avorio S. Knochel P. Synthesis  2000,  941 
• 9 Abarbri M. Thibonnet J. Bérillon L. Dehmel F. Rottländer M. Knochel P. J. Org. Chem.  2000,  65:  4618 
• 10 Kiesel M. Haug E. Kantlehner W. J. Prakt. Chem.  1997,  339:  159 
• 11 Garro-Helion F. Merzouk A. Guibé F. J. Org. Chem.  1993,  58:  6109