Benzotriazole mediated syntheses of α-fluoro-β-amino esters

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7063-7066

  Katritzky, Alan R ^a   Nichols, Daniel A ^a   Qi, Ming ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; ESTER; FLUORINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FLUORINATION; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032563958     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01520-2     Document Type: Article

References (12)

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3. (c) Angelastro, M. R.; Bey, P.; Mehdi, S.; Peet, N. P. Bioorg. Med. Chem. Lett. 1992, 2, 1235-1238.
4. 2. Taguchi, T.; Kitagawa, O.; Suda, Y.; Ohkawa, S.; Hashimoto, A.; Iitaka, Y.; Kobayashi, Y. Tetrahedron Lett. 1988, 29, 5291-5294.
5. 3. (a) Araki, K.; Wichtowski, J. A.; Welch, J. T. Tetrahedron Lett. 1991, 32, 5461-5464.
6. (b) Welch J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454-2462.
7. 4. (a) Fujisawa, T.; Hayakawa, R.; Shimizu, M. Tetrahedron Lett. 1992, 33, 7903-7906.
8. (b) Kaneko, S.; Yamazaki, T.; Kitazume, T. J. Org. Chem. 1993, 58, 2302-2312.
9. 5. Ishihara, T.; Ichihara, K.; Yamanaka, H. Tetrahedron 1996, 52, 255-262.
10. 6. Katritzky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Chem. Rev. 1998, 98, 409-548.
11. 3(aq) and filtered through Celite 545®. The layers were separated, and the aqueous phase was extracted with ether (3 × 10 mL). The combined organics were washed with 10 mL of brine, and dried over sodium sulphate. After the solvent was removed under reduced pressure, compounds 3, 5 were isolated by flash column chromatography (10:1 hexanes:ethyl acetate) of the crude product.
12. 4: C, 64.27 %; H, 6.74 %; N, 6.25 %. Found: C, 64.03 %; H, 6.97 %; N, 6.21 %.