Asymmetric O-methylhalohydrin reaction of chiral N-enoyl-2-oxazolidinones: Synthesis of N-protected syn-β-methoxyphenylalanine, an unusual amino acid component of cyclomarins

Tetrahedron Letters

Volumn 45, Issue 16, 2004, Pages 3185-3188

  Hajra, Saumen ^a   Karmakar, Ananta ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Halo methoxycarboxylic acid derivatives; Asymmetric; Halogen; N Enoyl 2 oxazolidinones; O Methylhalohydrin; Silver(I); syn Methoxyphenylalanine

Indexed keywords

AMINO ACID DERIVATIVE; HALIDE; HALOGEN; METHANOL; OXAZOLIDINE DERIVATIVE; PHENYLALANINE; PHENYLALANINE DERIVATIVE; SILVER;

AMINO ACID COMPOSITION; ARTICLE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 1642603935     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.131     Document Type: Article

References (32)

1. Zampella A., D'Auria M.V., Paloma L.G., Casapula A., Minale L., Debitus C., Henin Y. J. Am. Chem. Soc. 118:1996;6202.
2. Zampella A., Randazzo A., Borbone N., Luciani S., Trevisi L., Debitus C., D'Auria M.V. Tetrahedron Lett. 43:2002;6163.
3. Ford P.W., Gustafson K.R., McKee T.C., Shigematsu N., Maurizi L.K., Pannell L.K., Williams D.E., Silva E.D., Lassota P., Allen T.M., Soest R.V., Andersen R.J., Boyd M.R. J. Am. Chem. Soc. 121:1999;5899.
4. Renner M.K., Shen Y.C., Cheng X.C., Jensen P.R., Frankmoelle W., Kauffman C.A., Fencil W., Lobkovsky E., Clardy J. J. Am. Chem. Soc. 121:1999;11273.
5. Haruhiko T., Takehiko T., Yoshihiro T., Fumiaki H. Chem. Lett. 1992;431.
6. Dong L., Miller M.J. J. Org. Chem. 67:2002;3759.
7. Evans D.A., Ellman J.A., De Vries K.M. J. Am. Chem. Soc. 111:1989;8912.
8. Evans D.A., Weber A.E. J. Am. Chem. Soc. 109:1987;7151.
9. Tseng T.C., Wu M.J. Tetrahedron: Asymmetry. 6:1995;1622.
10. Nicolaou K.C., Kataoka T.C., Kumazawa T. J. Am. Chem. Soc. 110:1988;7910.
11. Sheehan J.C., Mania D., Nakamura S., Stock J.A. J. Am. Chem. Soc. 90:1968;362.
12. Tseng T.C., Wu M.J. Tetrahedron: Asymmetry. 6:1995;1622.
13. Boger D.L., Memezes R.F. J. Org. Chem. 57:1992;3221.
14. Aldol reaction: Evans D.A., Weber A.E. J. Am. Chem. Soc. 108:1986;6757.
15. Abdel-Magid A., Pridgen L.N., Eggleston D.S., Lantos I. J. Am. Chem. Soc. 108:1986;3595.
16. Evans D.A., Sjogren E.B., Weber A.E., Conn R.E. Tetrahedron Lett. 28:1987;29.
17. Pridgen L.N., Abdel-Magid A., Lantos I., Shilcart S., Eggleston D.S. J. Org. Chem. 58:1992;5107.
18. Catalytic enantioselective hydrogenation of α-chloro-β- ketoesters: Genet J.P., Andrade M.C.C., Vidal V.R. Tetrahedron Lett. 26:1995;2062.
19. Regioselective ring opening of epoxides: Bonini C., Righi G. Synthesis. 1993;225.
20. Righi G., Rumboldt G., Bonini C. Tetrahedron. 51:1995;12301.
21. Righi G., Chionne A., D'Achille R., Bonini C. Tetrahedron: Asymmetry. 8:1997;902.
22. Amantini D., Fringuelli F., Pizzo F., Vaccaro L. J. Org. Chem. 66:2001;3362.
23. House H.O. Modern Synthetic Reactions. 2nd ed. 1972;W. A. Benjamin, Menlo Park, CA. p 432.
24. March J. Advanced Organic Chemistry. 4th ed. 1992;Wiley, New York. p 815.
25. Carey F., Sundberg R. Advanced Organic Chemistry. 4th ed., Part B:2001;Plenum, New York. p 203.
26. Okamoto N., Hara O., Makino K., Hamada Y. J. Org. Chem. 67:2002;9210.
27. Boukhris S., Souizi A. Tetrahedron Lett. 40:1999;1669.
28. Bose G., Modal E., Khan A.T., Bordoloi M.J. Tetrahedron Lett. 42:2001;8907.
29. Kajigaeshi S., Masayuki M., Fujisaki S., Kakinami T., Okamto T. Bull. Chem. Soc. Jpn. 63:1990;3033.
30. Heasley V.L., Louie T.J., Luttrull D.K., Millar M.D., Moore H.B., Nogales D.F., Sauerbrey A.M., Shevel A.B., Shibuya T.Y., Stanley M.S., Shellhamer D.F., Heasley G.E. J. Org. Chem. 53:1988;2199.
31. Vishwakarma L.C., Walia J.S. J. Ind. Chem. Soc. 53:1976;156.
32. Crystallographic data (excluding structure factors) for the structure, have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 230141.