A new method for the α-vinylation of protected α-amino acids; ethylene oxide as vinyl cation equivalent

Synthetic Communications

Volumn 20, Issue 12, 1990, Pages 1819-1829

  Berkowitz, David B ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000340647     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397919008053106     Document Type: Article

References (12)

1. 1. Harvard University Traveling Scholar at the ETH in Zurich. Current address: Department of Chemistry, Yale University, P.O. Box 6666, New Haven, CT 06511, U.S.A.
2. For α-vinylglycine see: (a) Rando, R.R. Biochemistry, 1974,13, 3859; (b) Rando, R.R.; Relyea, N.; Cheng, L. J. Biol. Chem., 1976, 251, 3306; (c) Soper, T.S.; Manning, J.M.; Marcotte, P.A.; Walsh, C.T. Ibid., 1977, 252, 1571; (d) Cornell, N.W.; Zuurendonk, P.F.; Kerich, M.J.; Straight, C.B. Biochem. J., 1984,220, 707; (e) Griffith, O.W. J. Biol. Chem., 1983, 258, 1591; (f) Cho, C.; Ishii, R.; Hyeon, S.; Suzuki, A. Agric. Biol. Chem., 1987, 51, 2597.
3. For α-vinyl-DOPA, and α-vinyl-m-tyrosine see: (a) Maycock, A.L.; Aster, S.D.; Patchett, A.A. “Enzyme-Activated Irreversible Inhibitors,” ed. Seiler, N.et al., Elsevier, North Holland, 1978; pp. 211-220; (b) Maycock, A.L.; Aster, S.D.; Patchett, A.A. Developments in Biochemistry, 1979, 6, 115; (c) Jung, M.J.; Palfreyman, M.G.; Ribereau-Gayon, G.; Bey, P.; Metcalf, B.W.; Koch-Weser, J.; Sjoerdsma, A. Ibid., 1979, 6, 131; (d) Ribereau-Gayon, G.; Danzin, C.; Palfreyman, M.G.; Aubry, M.; Wagner, J.; Metcalf, B.W.; Jung, M.J. Biochem. Pharm., 1979, 28, 1331.
4. For a-vinylornithine see: Danzin, C.; Casara, P.; Claverie, N.; Metcalf, B.W. J. Med. Chem., 1981,24, 16.
5. For an example of competitive inhibition with α-vinylserine see: Tendler, S.J.B.; Threadgill, M.D.; Tisdale, M.J. J. Chem. Soc. Perkin Trans. l, 1987, 2617.
6. For α-vinylation approaches see: (a) Metcalf, B.W.; Bonilavri, E.; J. Chem. Soc. Chem. Commun., 1978, 914; (b) Steglich, W.; Wegmann, H. Synthesis, 1980, 481; (c) Sawada, S.; Nakayama, T.; Esaki, N.; Tanaka, H.; Soda, K.; Hill, R.K. J. Org. Chem., 1986,51, 3384; (d) Huldrik, P.F.; Kulkarni, A.S. J. Am. Chem. Soc., 1981, 103, 6251; (e) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409.
7. For alternative approaches see: (a) Taub, D.; Patchett, A.A. Tetrahedron Lett., 1977, 2725; (b) Metcalf, B.W.; Jund, K. Ibid., 1978, 3689; (c) Greenlee, W.J.; Taub, D.; Patchett, A.A. lbid, 1978, 3999; (d) Castelhano, A. L.; Horne, S.; Billedeau, R.; Krantz, A. Ibid., 1986, 27, 2435; (e) Munster, P.; Steglich, W. Synthesis, 1987, 223; (f) Castelhano, A.L.; Horne, S.; Taylor, G.J.; Billedeau, R.; Krantz, A. Tetrahedron, 1988, 44, 5451; (g) Vyas, D.M.; Chiang, Y.; Doyle, T.W. J. Org. Chem., 1984, 49,2037; (h) Fitzner, J.F.; Pratt, D.V.; Hopkins, P.B. Tetrahedron Lett., 1985, 26, 1959; (i) Hanessian, S.; Sahoo, S.P. lbid., 1984, 25, 1425; (j) Pellicciari, R.; Natalini, B.; Marinozzi, M. Syn. Commun., 1988, 18, 1715; (k) Rapoport, H.; Afzali-Ardakani, A. J. Org. Chem., 1980, 45, 4817; (1) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D.Helv. Chim. Acta, 1986, 69, 1365; and references 4 and 11.
8. There is one report of a direct vinylation of diethyl acetamidomalonate with ethylene and a Pd11 catalyst (ref. 4). However, the product, a previously well-characterized compound (see ref. 6c), was claimed to be “unstable”.
9. 9. Krapcho, A.P.; Dundulis, E.A. Tetrahedron Lett., 1976, 2205.
10. 10. Scarborough, R.M.; Smith, A.B.III Ibid., 1977, 4361.
11. 11. Barton, D.H.R.; Crich, D.; Herve, Y.; Potier, P.; Thiery, J. Tetrahedron, 1985,41, 4347.
12. 12. Brenner, M.; Huber, W. Helv. Chim. Acta, 1953, 36, 1109.