Synthesis of γ-fluoro-α-methyl-α-amino acids. A new alkylation procedure for ester imines

Tetrahedron

Volumn 54, Issue 22, 1998, Pages 5929-5938

  Haufe, Günter ^a   Laue, Klaus Wilhelm ^a   Triller, Michael Ulrich ^a   Takeuchi, Yoshio ^b   Shibata, Norio ^b  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Alkylation; Amino acids; Diastereoselection; Fluorine compounds

Indexed keywords

AMINO ACID DERIVATIVE; ESTER DERIVATIVE; IMINE;

ALKYLATION; AMINO ACID ANALYSIS; AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0032575220     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00292-0     Document Type: Article

References (22)

1. 1 Barrett GC, editor. Chemistry and Biochemistry of Amino Acids. New York: Chapman and Hall, 1985.
2. 2 O'Donnell MJ, Wu S. Tetrahedron: Asymmetry 1992;3:591-594.
3. 3 Heimgartner H. Angew. Chem. 1991;103:271-297; Angew. Chem. Int. Ed. Engl. 1991;30:238-264.
4. 3 Heimgartner H. Angew. Chem. 1991;103:271-297; Angew. Chem. Int. Ed. Engl. 1991;30:238-264.
5. 4 Seebach D, Sting AR, Hoffmann M. Angew. Chem. 1996;108:2881-2921; Angew. Chem. Int. Ed. Engl. 1996;35:2708-2748.
6. 4 Seebach D, Sting AR, Hoffmann M. Angew. Chem. 1996;108:2881-2921; Angew. Chem. Int. Ed. Engl. 1996;35:2708-2748.
7. 5 Chinchilla R, Falvello LR, Galindo N, Najera C. Angew. Chem. 1997;109:1036-1039; Angew. Chem. Int. Ed. Engl. 1997;36:995-997.
8. 5 Chinchilla R, Falvello LR, Galindo N, Najera C. Angew. Chem. 1997;109:1036-1039; Angew. Chem. Int. Ed. Engl. 1997;36:995-997.
9. 6 Welch JT. Tetrahedron 1987;43:3123-3197.
10. 7 Welch JT, Eswarakrishnan S. Fluorine in Bioorganic Chemistry. In: Fluorinated Amino Acids, New York: Wiley, 1991:7-65.
11. 8 Ojima I. New Developments in the Synthesis and Medicinal Applications of Fluoroamino Acids and Peptides. In: Filler R, Kobayashi Y, Yagupolskii LM, editors. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Amsterdam: Elsevier, 1993:241-273.
12. 9 Kukhar VP, Soloshonok VA, editors. Fluorine Containing Amino Acids. Chichester: Wiley, 1995.
13. 10 Haufe G, Kröger S. Amino Acids 1996;11:409-424.
14. 11 McGuire JJ, Haile WH, Bey P, Coward JK. J. Biol. Chem. 1990;265:14073-14079.
15. 12 Leutbecher U, Bocher R, Linder D, Buckel W. Eur. J. Biochem. 1992;205:759-765.
16. 13 Kröger S, Haufe G. Amino Acids 1997;12:363-372.
17. 14 Kröger S, Haufe G. Liebigs Ann./Recl. 1997:1201-1206.
18. 15 The bromofluoroalkanes 2 (X=Br) were synthesized by bromofluorination of the corresponding 1-alkenes (Alvernhe G, Laurent A, Haufe G, Synthesis 1987;562-564) while the iodofluoroalkanes 2 (X=I) were obtained from the bromo compounds by Finkelstein reaction.
19. 16 Laue KW, Haufe G. Synthesis 1998, accepted.
20. 17 O'Donnell MJ, Poll RL. J. Org. Chem. 1982;47:2663-2666.
21. 18 Schmeck C, Hegedus LS. J. Am. Chem. Soc. 1994;116:9927-9934.
22. 19 Baldwin JE, Moloney MG, North M. Tetrahedron 1989;45:6319-6330.