Practical and efficient route to (S)-γ-fluoroleucine

Synlett

Volumn , Issue 8, 2005, Pages 1279-1280

  Truong, Vouy Linh ^a   Gauthier, Jacques Yves ^a   Boyd, Michael ^a   Roy, Bruno ^a   Scheigetz, John ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

(S) fluoroleucine; Continuous liquid liquid extraction; Methylmagnesium bromide; N,N diethylaminosulfur trifluoride; Oxazolidinone

Indexed keywords

AMINO ACID DERIVATIVE; AMINOALCOHOL; CARBONYL DERIVATIVE; GAMMA FLUOROLEUCINE; LEUCINE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; FLUORINATION; LIQUID LIQUID EXTRACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 19944396469     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-868494     Document Type: Article

References (30)

1. For reviews, see: (a) Kollonitsch, J.; Patchett, A. A.; Marburg, S.; Maycock, A. L.; Perkins, L. M.; Doldouras, G. A.; Duggan, D. E.; Aster, S. D. Nature 1978, 274, 906.
2. (b) Welch, J. T. Tetrahedron 1987, 43, 3123.
3. (c) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991.
4. (d) Papageorgiou, C.; Borer, X.; French, R. R. Bioorg. Med. Chem. Lett. 1994, 4, 267.
5. (e) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V. P.; Soloshonok, V. A., Eds.; Wiley: Chichester, UK, 1995.
6. (f) Filler, R.; Kobayashi, Y. Biomedical Aspect of Fluorine Chemistry; Elsevier Biomedical Press: Amsterdam, The Netherlands, 1982.
7. (g) Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Elsevier Biomedical Press: Amsterdam, The Netherlands, 1993.
8. (h) Marsh, E. N. G. Chem. Biol. 2000, 7, R153.
9. (i) Tsukamoto, T.; Coward, J. K. J. Org. Chem. 1996, 61, 2497.
10. (a) Ramesh, B.; Edward, K. H.; Krishma, K. J. Org. Chem. 2004, 69, 5468.
11. (b) Anderson, J. T.; Toogood, P. L.; Marsh, E.; Neil, G. Org. Lett. 2002, 4, 4281.
12. (c) Xing, X.; Fichera, A.; Krishna, K. Org. Lett. 2001, 3, 1285.
13. (d) Renner, C.; Alefelder, S.; Bae, J. H.; Budisa, N.; Huber, R.; Moroder, L. Angew. Chem. Int. Ed. 2001, 40, 923.
14. (e) Tang, Y.; Ghirlanda, G.; Petka, W. A.; Nakajima, T.; Degrado, W. F.; Tirrell, D. A. Angew. Chem. Int. Ed. 2001, 40. 1494.
15. (f) Tang, Y.; Tirrell, D. A. J. Am. Chem. Soc. 2001, 123, 11089.
16. (g) Bretscher, L. E.; Jenkins, C. L.; Taylor, K. M.; DeRider, M. L.; Raines, R. T. J. Am. Chem. Soc. 2001, 123, 777.
17. (h) Holmgren, S. K.; Taylor, K. M.; Bretscher, L. E.; Raines, R. T. Nature 1998, 392, 666.
18. (i) Qing, F.-L.; Peng, S.; Hu, C.-M. J. Fluorine Chem. 1998, 88, 79.
19. (j) Welch, J. T. Tetrahedron 1987, 43, 3123.
20. (k) Qiu, X. L.; Meng, W. D.; Qing, F. L. Tetrahedron 2004, 60, 6711.
21. Limanto, J.; Shafiee, A.; Devine, P. N.; Upadhyay, V.; Desmond, R. A.; Foster, P. R.; Gauthier, D. R.; Reamer, R. A.; Volante, R. P. J. Org. Chem. 2005, 70, 2372.
22. Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; Martinez, J. Tetrahedron Lett. 1991, 32, 923.
23. For reviews on the conversion of alcohols to alkyl fluorides: (a) Middleton, W. J. J. Org. Chem,. 1975, 40, 574.
24. (b) Middleton, W. J.; Bingham, E. M. Org. Synth., Coll. Vol. VI; Wiley and Sons: New York, 1988, 835.
25. (c) Hudlicky, M. Org. React. 1988, 55, 513.
26. Zhao, H.; Thurkauf, A. Synlett 1999, 1280.
27. Ghosk, A. K.; Kincaid, J. F.; Haske, M. G. Synthesis 1997, 541.
28. (a) Zhao, M.; Li, J.; Song, Z.; Desmond, R.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 1998, 39, 5323.
29. (b) Reginato, G.; Mordini, A.; Valcchi, M.; Grandini, E. J. Org. Chem. 1999, 64, 9211.
30. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.