Synthesis of (2S,3R)-3-Amino-2-Hydroxy-5-Methylhexanoic Acid: Bridging Effect of KF

Journal of Organic Chemistry

Volumn 55, Issue 15, 1990, Pages 4750-4754

  Solladie Cavallo, A ^a   Khiar, N ^a  

^a EHICS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000895514     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00302a050     Document Type: Article

References (31)

1. Tobe, H.; Morishima, H.; Naganawa, H.; Takita, T.; Aoyagi, T.; Umezawa, H. Agr. Biol. Chem. 1979, 43, 591.
2. Aoyagi, T.; Tobe, H.; Kojma, F.; Hamada, M.; Takeuchi, T.; Umezawa, H. J. Antiobiot. 1978, 31, 221.
3. Iizuka, K.; Kamijo, T.; Kubota, T.; Akahane, K.; Umeyama, H.; Kiso, Y. J. Med. Chem. 1988, 31, 701.
4. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H.; Aoyagi, T.; Umezawa, H. J. Med. Chem. 1977, 20, 510.
5. Rich, D. H.; Moon, B. J.; Boparai, A. S. J. Org. Chem. 1980, 45, 2288.
6. Johnson, R. L. J. Med. Chem. 1982, 25, 605.
7. Inversion of diastereoselectivity comes from differences in mechanisms.
8. Chong, J. M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1563.
9. Solladie-Cavallo, A.; Lapitajs, G.; Buchert, P.; Klein, A.; Colonna, S.; Manfredi, A. J. Organomet. Chem. 1987, 330, 357.
10. Solladie-Cavallo, A.; Khiar, N. Tetrahedron. Lett. 1988,29, 2189.
11. Henry, L.; Hebd, L. C. Seances Akad. Sci. 1985,120. 1265.
12. Williams, T. M.; Crumbie, R.; Mosher, H. S. J. Org. Chem. 1985, 50. 91.
13. Seebach, D.; Beck, A. K.; Mukhopadhay, T.; Thomas, E. Helv. Chim. Acta 1982, 65, 1101.
14. Eyer, M.; Seebach, D. J. J. Am. Chem. Soc. 1985, 107, 3601.
15. Wollenberg, R. H.; Miller, S. J. Tetrahedron Lett. 1978, 3219.
16. Melot, J. M.; Texier-Boulet, F.; Foucaud, A. Tetrahedron Lett. 1986, 27, 493.
17. For the use of 8-phenylmenthyl glyoxylate as chiral substrate, see: Whitesell, J. K.; Allen, D. E. J. Am. Chem. Soc. 1988, 110, 3585 and references therein.
18. Jurczak, J.; Zamojski, A. Ann. Soc. Chim. Polonorum 1977, 44, 2257.
19. Khair, N. Thesis, Strasbourg, December 1989.
20. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
21. (-)-8-Phenylmenthol is recovered during hydrolysis (step 6 Scheme I) through ether extraction of the acidic aqueous phase.
22. Solladie-Cavallo, A.; Khiar, N. Synth. Commun. 1989, 19, 1335.
23. Futagawa, S.; Inui, T.; Shiba, T. Bull. Chem. Soc. Jpn. 1973, 46, 3308.
24. Meyers, A. I.; Knaus, G.; Kamata, K.; Ford, M. E. J. Am. Chem. Soc. 1976, 98, 567.
25. It is also known that in TBAF/THF, F- can be considered more naked than in KF hydrates, which makes it a stronger base.
26. 18-Crown-6, especially suited to complex potassium ions, increases the solubility of KF and the reactivity of the anion F-, see: Synthetic Multidentate Macrocyclic Compounds; Izatt, R. M., Christensen, J. J., Eds.; Academic Press: San Francisco. 1978: p 111.
27. Asymmetric Synthesis; Morrison, J. D., Eds.; Academic Press: New York, 1984; vol 3,p 80 (D. A. Evans).
28. In complex KF-4I the small H atom points toward the phenyl ring and the isobutyl group is away from the menthyl ring.
29. Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908.
30. Vedeis, E. Organic Synthesis INC. 1987. 65. 203.
31. Gilbert, K. E.; Borden, W. T. J. Org. Chem. 1979, 44, 659.