Intramolecular S(N)2 reaction at α-carbon of trifluoromethyl group: Preparation of optically active 2-trifluoromethylaziridine

Tetrahedron Asymmetry

Volumn 8, Issue 17, 1997, Pages 2933-2937

  Katagiri, Toshimasa ^a   Ihara, Hideki ^a   Takahashi, Mikihiro ^a   Kashino, Setsuo ^a   Furuhashi, Keizo ^b   Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

^b JAPAN ENERGY CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 TRIFLUOROMETHYLAZIRIDINE; AZIRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; HYDROXYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030766925     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00320-0     Document Type: Article

References (15)

1. a) Fluorine-containing Amino Acids Synthesis and Properties; Kukhar, V. P.; Soloshonok, V. A., Eds.; John Wiley & Sons: New York, 1995.
2. b) Fluorine in Bioorganic Chemistry; Welch, J. T.; Eswarakrishnan, S; John Wiley & Sons, New York, 1991.
3. a) Chemistry of Organic Fluorine Compounds II; Hudlicky, M.; Pavlath, A. E., Eds.; American Chemical Society, 1995.
4. b) Fluorine Chemistry; Smart, B. E. Eds.; Chem. Rev. 1996, 96, 1555.
5. a) Bussche-Hunnefeld, C. von dem; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795.
6. b) Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41.
7. Furuhashi, K., in Chirality in Industry; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; John Wiley & Sons, 1992, p. 167.
8. a) Klaubunde, K. J.; Burton, D. J. J. Am. Chem. Soc. 1972, 94, 5985.
9. b) Ullmann, J.; Hanack, M. Synthesis 1989, 685.
10. c) Katagiri, T. Jpn. Kokai Tokkyo Koho JP 08-27044, 1996.
11. Hagiwara, T.; Tanaka, K.; Fuchikami, T. Tetrahedron Lett. 1996, 37, 8187.
12. Shinohara, N; Yamazaki, T.; Kitazume, T. Rev. Heteroatom Chem. 1996, 14, 165.
13. The optically active (S)-3,3,3-trifluoropropene oxide is commercially available from the Japan Energy Corporation.
14. a) Appel, R.; Kleinstück, R. Chem. Ber. 1974, 107, 5.
15. b) Okada, I.; Ichimura, K.; Sudo, R. Bull. Chem. Soc. Jpn. 1970, 43, 1185.