Abstract
Protected α-Phenyl glycine17 and phenylalanine18 and19 have been synthesized through an efficient three-step sequence from the corresponding allyl ethers5, 7, and10. The key intermediate in this synthesis is the corresponding allylic amines prepared by reaction of allyl ethers with chlorosulfonyl isocyanate.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Barrett, G. C. and Elmore, D. T., Amino Acids and Peptides. Cambridge University Press. pp 123–125 (1998).
Greene, T. W. and Wuts, P. G. M., Protective Groups in organic Synthesis (3rd). John Wiley & Sons Inc., pp 502–503 (1999).
Harada, K., Asymmetric Synthesis. ed Morrison, J. D., Academic Press, New York, Vol. 5, pp 345 (1985).
Hayashi, T., Yamamoto, A., Ito, Y., Nishioka, E., Miura, H. and Yanagi, K., Asymmetric Synthesis Catalyzed by Chiral Ferrocenylphosphine-Trandition-Metal Complexes. 8. Palladium-Catalyzed Asymmetric Allylic Amination.J. Am. Chem. Soc., 111, 6301–6311 (1989).
Kim, J. D., Lee, M. H., Lee, M.J., and Jung, Y.H., Novel Synthetic Method for N-Allylcarbamates from Allyl ethers using Chlorosulfonyl isocyanate.Tetrahedron Lett., 41, 5073–5076 (2000).
Mooiweer, H. H., Hiemstra, H., and Speckarap, W. N., Synthesis of γδ-Unsaturated α-Amino Acids from Allylsilanes and Glycidyl cation equivalents.Tetrahedron, 45, 4627–4636 (1989).
Oppolzer, W., and Moretti, R., Enantioselective Syntheses of α-Amino acids from 10-Sulfonamide-isobornyl esters and DL-t-Butyl azodicarboxylate.Tetrahedron, 44, 5541–5552 (1988).
Rao, Y. S., and Filler, R., Geometric isomers of 2-Aryl (Aralkyl)-4-arylidene(alkylidene)-5(4H)-oxazolones.Synthesis, 749–764 (1975).
Rose, C. B., and Taylor, S. K., Reaction of Organometallic Reagents with Unsaturated Epoxides. II. Control of Product Ratio.J. Org. Chem., 39, 578–581 (1974).
Rychnovsky, S. D., Skalitzky, D. J., Pathirana, C., Jesen, P. R. and Fenical, W., Stereochemistry of the Macrolactins.J. Am. Chem. Soc., 114, 671–677 (1992).
Ugi, I., Marquarding, D., and Urban, R., Chemistry and Biochemistry of Amino Acids, Peptides & Proteins. ed Weinstein, B., Dekker, New York. Vol. 6, pp 245 (1982).
Williams, Synthesis of Optically Active α-Amino Acids. Pergamon, Elmsford, NY, pp 208–229 (1989).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Jung, Y.H., Kim, J.D. A novel synthetic methods for α-amino acids from allyl ethersvia N-Allylcarbamates. Arch Pharm Res 23, 574–578 (2000). https://doi.org/10.1007/BF02975243
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02975243