Simple and Efficient Multigram Scale Synthesis of 1-Aminocyclopent-3-ene-1-carboxylic Acid

Abstract

A very simple and inexpensive synthesis of the valuable intermediate 1-aminocyclopent-3-ene-1-carboxylic acid on a multigram scale and with a high overall yield (80%) is reported. The efficiency of the procedure relies on the ready accessibility and high reactivity of the glycine equivalent used as the starting material.

Key words

allylations - amino acids - heterocycles - metathesis - ring closure

References

• The selective synthesis of quaternary α-amino acids has been reviewed:
• 1a Cativiela C. Díaz-de-Villegas MD. Tetrahedron: Asymmetry  1998,  9:  3517 
• 1b Cativiela C. Díaz-de-Villegas MD. Tetrahedron: Asymmetry  2000,  11:  645 
• 2a Cowell SM. Lee YS. Cain JP. Hruby VJ. Curr. Med. Chem.  2004,  11:  2785 
• 2b Toniolo C. Crisma M. Formaggio F. Peggion C. Biopolymers (Pept. Sci.)  2001,  60:  396 
• 2c Venkatraman J. Shankaramma SC. Balaram P. Chem. Rev.  2001,  101:  3131 
• 2d Benedetti E. Biopolymers (Pept. Sci.)  1996,  40:  3 
• 3 Ohwada T. Kojima D. Kiwada T. Futaki S. Sugiura Y. Yamaguchi K. Nishi Y. Kobayashi Y. Chem. Eur. J.  2004,  10:  617 
• 4 Tanaka M. Demizu Y. Doi M. Kurihara M. Suemune H. Angew. Chem. Int. Ed.  2004,  43:  5360 
• 5a Moloney MG. Nat. Prod. Rep.  2002,  19:  597 
• 5b Monn JA. Schoepp DD. Annu. Rep. Med. Chem.  2000,  35:  1 
• 5c Pellicciari R. Costantino G. Curr. Opin. Chem. Biol.  1999,  3:  433 
• 6a Conti P. De Amici M. Bräuner-Osborne H. Madsen U. Toma L. De Micheli C. Farmaco  2002,  57:  889 
• 6b Conti P. De Amici M. Joppolo-di-Ventimiglia S. Stensbol TB. Madsen U. Bräuner-Osborne H. Russo E. De Sarro G. Bruno G. De Micheli C. J. Med. Chem.  2003,  46:  3102 
• 6c Roda G. Conti P. De Amici M. He J. Polavarapu PL. De Micheli C. Tetrahedron: Asymmetry  2004,  15:  3079 
• 7 Hammer K. Wang J. Falck-Pedersen ML. Romming C. Undheim K. J. Chem. Soc., Perkin Trans. 1  2000,  1691 
• 8 Amori L. Costantino G. Marinozzi M. Pellicciari R. Gasparini F. Flor PJ. Kuhn R. Vranesic I. Bioorg. Med. Chem. Lett.  2000,  10:  1447 
• 9a Hodgson DM. Thompson AJ. Wadman S. Tetrahedron Lett.  1998,  39:  3357 
• 9b Hodgson DM. Thompson AJ. Wadman S. Keats CJ. Tetrahedron  1999,  55:  10815 
• 10 Deprés JP. Greene AE. J. Org. Chem.  1984,  49:  928 
• 11 Larionov OV. Kozhushkov SI. de Meijere A. Synthesis  2005,  158 
• 12 Doller D. Chackalamannil S. Stamford A. McKittrick B. Czarniecki M. Bioorg. Med. Chem. Lett.  1997,  7:  1381 
• 13a Park K.-H. Olmstead MM. Kurth MJ. J. Org. Chem.  1998,  63:  113 
• 13b Park K.-H. Olmstead MM. Kurth MJ. J. Org. Chem.  1998,  63:  6579 
• 13c Park K.-H. Kurth TM. Olmstead MM. Kurth MJ. Tetrahedron Lett.  2001,  42:  991 
• 14 Hammer K. Undheim K. Tetrahedron  1997,  53:  2309 
• 15a Kotha S. Sreenivasachary N. Bioorg. Med. Chem. Lett.  1998,  8:  257 
• 15b Kotha S. Sreenivasachary N. Mohanraja K. Durani S. Bioorg. Med. Chem. Lett.  2001,  11:  1421 
• 16 Grubbs RH. Handbook of Metathesis   Wiley; New York: 2003. 
• 17 Cativiela C. Díaz-de-Villegas MD. 5(2H)-Oxazolones and 5(4H)-Oxazolones, In Oxazoles: Synthesis, Reactions and Spectroscopy. The Chemistry of Heterocyclic Compounds   Part B, Vol. 60:  Palmer DC. Wiley; New York: 2004.  p.129-330  
• 18 Akashi H. Yuki Gosei Kagaku Kyokai Shi  1975,  33:  483 ; Chem. Abstr. 1975, 83, 193143