DOI: 10.1039/A906223H
(Paper)
Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 2659-2660
A one-pot three-component synthesis of β-nitro-α-amino acids and their N-alkyl derivatives
(Note: The full text of this document is currently only available in the PDF Version )
Phillip A. Coghlan and Christopher J. Easton
Abstract
A water-based condensation of glyoxylic acid, nitroalkanes and amines is described, offering a straightforward synthesis of β-nitro-α-amino acids and their N-alkyl derivatives.
References
- I. Ugi, J. Prakt. Chem., 1997, 339, 499 CAS.
- G. Dyker, Angew. Chem., Int. Ed. Engl., 1997, 36, 1700 CAS.
- T. A. Alston, D. J. T. Porter and H. J. Bright, Acc. Chem. Res., 1983, 16, 418 CrossRef CAS.
- V. A. Burgess and C. J. Easton, Aust. J. Chem., 1988, 41, 1063 CAS.
- C. J. Easton, P. D. Roselt and E. R. T. Tiekink, Tetrahedron, 1995, 51, 7809 CrossRef CAS; P. A. Coghlan and C. J. Easton, Tetrahedron Lett., 1999, 40, 4745 CrossRef CAS.
- A. J. Hoefnagel, H. van Bekkum and J. A. Peters, J. Org. Chem., 1992, 57, 3916 CrossRef CAS.
- M. Arend, B. Westermann and N. Risch, Angew. Chem., Int. Ed., 1998, 37, 1045 CrossRef.
- P. A. Grieco, S. D. Larsen and W. F. Fobare, Tetrahedron Lett., 1986, 27, 1975 CrossRef CAS.
- For example see: X. L. Armesto, M. Canle, L. M. V. García and J. A. Santaballa, Chem. Soc. Rev., 1998, 27, 453 Search PubMed.
- P. A. Grieco, Organic Synthesis in Water, Blackie Academic & Professional Press, London, 1998 Search PubMed; A. Lubineau, J. Augé and Y. Queneau, Synthesis, 1994, 741 Search PubMed.
- H. H. Baer and L. Urbas, in The Chemistry of the Nitro and Nitroso Groups. Part 2, ed. H. Feuer, Interscience Publishers, New York, 1970, p. 75 Search PubMed.