A novel stereoselective synthesis of cis-2-fluoro-cyclopropane-1-carboxylic acid

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8507-8510

  Toyota, Akemi ^c   Ono, Yoshinori ^b   Kaneko, Chikara ^b   Hayakawa, Isao ^a  

^a DAIICHI SANKYO CO   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANECARBOXYLIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; FLUORINATION; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0000566323     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01952-1     Document Type: Article

References (19)

1. 1. a) Kimura, Y.; Atarashi, S.; Kawakami, K.; Sato, K.; Hayakawa, I. J. Med. Chem. 1994, 37, 3344-3352.
2. b) Atarashi, S.; Imamura, M.; Kimura, Y.; Yoshida, A.; Hayakawa, I. J. Med. Chem. 1993, 36, 3444-3448.
3. 2. For racemic synthesis, see Tamura, O.; Hashimoto, M.; Kobayashi, Y.; Katoh, T.; Nakatani, K.; Kamada, M.; Hayakawa, I.; Akiba, T.; Terashima, S. Tetrahedron 1994, 50, 3889-3904. For asymmetric synthesis, see Akiba, T.; Tamura, O.; Hashimoto, M.; Kobayashi, Y.; Katoh, T.; Nakatani, K.; Kamada, M.; Hayakawa, I.; Terashima, S. Tetrahedron 1994, 50, 3905-3914.
4. 2. For racemic synthesis, see Tamura, O.; Hashimoto, M.; Kobayashi, Y.; Katoh, T.; Nakatani, K.; Kamada, M.; Hayakawa, I.; Akiba, T.; Terashima, S. Tetrahedron 1994, 50, 3889-3904. For asymmetric synthesis, see Akiba, T.; Tamura, O.; Hashimoto, M.; Kobayashi, Y.; Katoh, T.; Nakatani, K.; Kamada, M.; Hayakawa, I.; Terashima, S. Tetrahedron 1994, 50, 3905-3914.
5. 3. a) Hayakawa, I.; Atarashi, S.; Kimura, Y.; Kawakami, K.; Saito, T.; Yafune, T.; Sato, K.; Une, K.; Sato, M. 31st Interscience Conference on Antimicrobial Agents and Chemoterapy, Chicago, 1991; Abstract No. 1504.
6. b) Hayakawa, I.; Kimura, Y. Japan Kokai Tokkyo Koho 1990, JP2-231475.
7. c) Hayakawa, I.; Kimura, Y. Japan Kokai Tokkyo Koho 1991, JP3-291258.
8. 4. Mousseron, M.; Fraisse, R. Compt. rend. 1959, 248, 887-889.
9. 5. McCoy, L. L. J. Am. Chem. Soc. 1958, 80, 6568-6572; McCoy, L. L. J. Org. Chem. 1960, 25, 2078-2082.
10. 5. McCoy, L. L. J. Am. Chem. Soc. 1958, 80, 6568-6572; McCoy, L. L. J. Org. Chem. 1960, 25, 2078-2082.
11. 6. a) The diastereoisomeric pure sulfoxide (cis-6) was also obtained in 51% yield by the same reaction using NaH in THF at room temperature.
12. tBu in THF at 0 °C→ room temperature. Under these conditions, initially formed cis-6 was observed to isomerize to trans-6 by tlc analysis.
13. 7. Toyota, A.; Ono, Y.; Chiba, J.; Sugihara, T.; Kaneko, C. Chem. Pharm. Bull. 1996, 44, 703-708. See also, Chiba, J.; Sugihara, T.; Kaneko, C. Chem. Lett. 1995, 581-582.
14. 7. Toyota, A.; Ono, Y.; Chiba, J.; Sugihara, T.; Kaneko, C. Chem. Pharm. Bull. 1996, 44, 703-708. See also, Chiba, J.; Sugihara, T.; Kaneko, C. Chem. Lett. 1995, 581-582.
15. 8. In Pummerer reaction of arylsulfinylcyclopropanes with acetic anhydride giving 1-phenylthio-1-acetoxycyclopropanes, the acetate anion attacked the α-carbon predominantly from the back side of the proton removed. A similar mechanism involving initial formation of sulfurane-like intermediate (cf. B) followed by subsequent intramolecular acetoxy migration was proposed. Masuda, T.; Numata, T.; Furukawa, N.; Oae, S. J. C. S. Perkin II 1978, 1302-1308. See also a review for the Pummerer reaction of sulfinyl compounds, Lucch, O. D. Organic Reactions 1991, 40, Chap. 3, 157-405.
16. 8. In Pummerer reaction of arylsulfinylcyclopropanes with acetic anhydride giving 1-phenylthio-1-acetoxycyclopropanes, the acetate anion attacked the α-carbon predominantly from the back side of the proton removed. A similar mechanism involving initial formation of sulfurane-like intermediate (cf. B) followed by subsequent intramolecular acetoxy migration was proposed. Masuda, T.; Numata, T.; Furukawa, N.; Oae, S. J. C. S. Perkin II 1978, 1302-1308. See also a review for the Pummerer reaction of sulfinyl compounds, Lucch, O. D. Organic Reactions 1991, 40, Chap. 3, 157-405.
17. 5 (L: ligand) and HOMO of C-H] is not important, because MO amplitudes of axial ligands in the former are very small. Hoffmann, R.; Howell, J. M.; Muetterties, E. L. J. Am. Chem. Soc. 1972, 94, 3047-3058.
18. 10. Obviously, cis-D should be less stable than trans-D. Hence, while trans-6 affords stereoselectively trans-8 via trans-D, cis-6 gives trans-8 as the major product through inversion of initially formed cis-D to trans-D (cf. Table 1).
19. 11. Lee, G. H.; Choi E. B.; Lee, E.; Pak, C. S.Tetrahedron Lett. 1993, 4541-4542.