Asymmetric synthesis of α-allenylglycines

European Journal of Organic Chemistry

Volumn , Issue 21, 2009, Pages 3605-3612

  Bucuroaia, Carmen ^a   Groth, Ulrich ^a   Huhn, Thomas ^a   Klinge, Michael ^b  

^a UNIVERSITY OF KONSTANZ   (Germany)

^b GIT Verlag GmbH and Co KG   (Germany)

Author keywords

Alkynes; Allenes; Amino acids; Asymmetric synthesis; Cuprates

Indexed keywords

EID: 67650697115     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900462     Document Type: Article

References (36)

1. C. Angst, Pure Appl. Chem. 1987, 59, 373-380.
2. D. B. Berkowitz, B. D. Charette, K. R. Karakurichi, J. M. McFadden. Tetrahedron: Asymmetry 2006, 17, 869-882.
3. C. Walsh, Tetrahedron 1982, 38, 871-909.
4. A. L. Castelhano, D. H. Pliura, G. J. Taylor, K. C. Hsieh, A. Krantz, J. Am. Chem. Soc. 1984, 106, 2734-2735.
5. P. Friis, P. Helboe, P. O. Larsen, Acta Chem. Scand., Sen B 1974, 28, 317-321.
6. R. M. Williams, D. J. Aldous, S. C. Aldous, J. Org. Chem. 1990, 55, 4657-4663.
7. J.-X. Ji, T. T.-L. Au-Yeung, J. Wu, C. W. Yip, A. S. C. Chan, Adv. Synth. Catal. 2004, 346, 42-44.
8. A. L. Castelhano, S. Home, G. J. Taylor, R. Billedeau, A. Krantz, Tetrahedron 1988, 44, 5451-5466.
9. U. Schollkopf, U. Groth, Angew. Chem. 1981, 93, 1022-1023.
10. U. Groth, U. Schollkopf, Y.-C. Chiang, Synthesis 1982, 864-866.
11. U. Schöllkopf, J. Nozulak, U. Groth, Tetrahedron 1984, 40, 1409-1417.
12. For a review for the asymmetric synthesis of vinylglycines, see: R. M. Williams, Synthesis of Optically Active a-Amino Acids, Pergamon Press, Oxford, 1989.
13. W. Karnbrock, H.-J. Musiol, L. Moroder, Tetrahedron 1995, 51, 1187-1196.
14. S. Rodbotten, T. Benneche, K. Undheim, Acta Chem. Scand. 1997, 51, 873-880.
15. U. Schollkopf, U. Groth, C. Deng, Angew. Chem. 1981, 93, 793-795.
16. G. C. Barrett (Ed.), Chemistry and Biochemistry of the Amino Acids, Chapman and Hall, London, 1985.
17. A. Hoffmann-Röder, N. Krause, Angew. Chem. Int. Ed. 2004, 43, 1196-1216.
18. P. Casara, K. Jund, P. Bey, Tetrahedron Lett. 1984, 25, 1891-1894.
19. U. Kazmaier, C. H. Goerbitz, Synthesis 1996, 1489-1493.
20. U. Kazmaier, Liebigs Annalenl Recueil 1997, 1997, 285-295.
21. M. P. Doyle, V. Bagheri, E. E. Claxton, J. Chem. Soc, Chem. Commim. 1990, 46-48.
22. D. P. G. Hamon, R. A. Massy-Westropp, P. Razzino, Tetrahedron 1995, 51, 4183-4194.
23. H. Kagoshima, T. Uzawa, T. Akiyama, Chem. Lett. 2002, 298-299.
24. J. L. Luche, E. Barreiro, J. M. Dollat, P. Crabbe. Tetrahedron Lett. 1975, 16, 4615-4618.
25. Organometallic Derivatives of Allenes and Ketenes, J.-L. Moreau, in The Chemistry of Ketenes. Allenes. and Related Compounds (Ed.: S. Patai). Wiley-VCH, New York, 1980, vol. 1. p. 363-413.
26. II. Yamamoto, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford. 1992, Vol. 2. pp. 81-98.
27. Synthesis and Reaction of Allenylmetal Compounds, J. A. Marshall, B. W. Gung, M. L. Grachan, in: Modern Allene Chemistry (Eds.: N. Krause, A. S. K. Hashmi). Wiley-VCH. Weinheim. Germany. 2004. pp. 493-592.
28. E. J. Corey, D. Enders, Chem. Ber. 1978, 111, 1362-1383.
29. K. Yamamoto, M. Iijima, Y. Ogimura, Tetrahedron Lett. 1982, 23, 3711-3714.
30. T. Beulshausen, U. Groth, U. Schollkopf, Liebigs Ann. Chem. 1991, 1991, 1207-1209.
31. U. Schöllkopf, Tetrahedron 1983, 39, 2085-2091.
32. U. Groth, Ph.D. Thesis, University of Göttingen, 1982.
33. cyclo-(-L-Val-Gly-) [(2S)-(+)-2,5-dihydro-3,6-dimethoxy-2-iso- propylpyrazin] and its enatiomeric form are available from Merck International (http://www.merck-chemicals.com).
34. C. Bucuroaia, planned Ph.D. Thesis, University of Konstanz.
35. L. Brandsma, H. D. Verkruijsse, Synthesis of Acetylenes, Allenes and Cumulenes, A. Laboratory Manual, Elsevier, Amsterdam, 1981
36. K. E. Schulte, K. P. Reiss, Chem. Ber. 1954, 87, 964-970.