The preparation of enantiomerically pure cyclopropylalanine

Tetrahedron Asymmetry

Volumn 14, Issue 22, 2003, Pages 3575-3580

  Boaz, Neil W ^a   Debenham, Sheryl D ^a   Large, Shannon E ^a   Moore, Mary K ^a  

^a EASTMAN CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE DERIVATIVE; CYCLOPROPANE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CRYSTALLIZATION; ENANTIOMER; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0242710812     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.07.007     Document Type: Article

References (25)

1. For recent reviews, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 1-110; (b) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfalz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. I, pp. 121-182.
2. For recent reviews, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 1-110; (b) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfalz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. I, pp. 121-182.
3. Knowles, W. S.; Sabacky, M. J. US Patent 4124533, 1978 Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952 and references cited therein.
4. Landis C.R., Halpern J. J. Am. Chem. Soc. 109:1987;1746-1754.
5. Chua P.S., Roberts N.K., Bosnich B., Okrasinski S.J., Halpern J. J. Chem. Soc., Chem. Commun. 1981;1278-1280.
6. Chan A.S.C., Pluth J.J., Halpern J. J. Am. Chem. Soc. 102:1980;5952-5954.
7. Chan A.S.C., Halpern J. J. Am. Chem. Soc. 102:1980;838-840.
8. Halpern J., Riley D.P., Chan A.S.C., Pluth J.J. J. Am. Chem. Soc. 99:1977;8055-8057.
9. Wehner, V.; Flohr, S.; Blum, H.; Ruetten, H.; Stilz, H. U. PCT Int. Appl. WO 0311288, 2003.
10. Lynch C.L., Hale J.J., Budhu R.J., Gentry A.L., Mills S.G., Chapman K.T., MacCoss M., Malkowitz L., Springer M.S., Gould S.L., Demartino J.A., Danzeisen R., Hazuda D., Kessler J., Lineberger J., Miller M., Emini E.A. Bioorg. Med. Chem. Lett. 12:2002;3001-3004 Hanson, G. J.; Chen, B. B.; Baran, J. S. U.S. Patent 5268391, 1993 Christensen, J. V.; Kristensen, E. PCT Int. Appl. WO 0176636, 2001 Wehner, V.; Stilz, H. U.; Schmidt, W.; Seiffge, D. PCT Int. Appl. WO 0069831, 2000.
11. Myers A.G., Schnider P., Kwon S., Kung D.W. J. Org. Chem. 64:1999;3322-3327.
12. Myers A.G., Gleason J.L., Yoon T., Kung D.W. J. Am. Chem. Soc. 119:1997;656-673.
13. Corey E.J., Xu F., Noe M.C. J. Am. Chem. Soc. 119:1997;12414-12415.
14. Hamon C., Rawlings B.J. Synth. Commun. 26:1996;1109-1115.
15. Chenault H.K., Dahmer J., Whitesides G.M. J. Am. Chem. Soc. 111:1989;6354-6364.
16. Ohta T., Nakajima S., Sato Z., Aoki T., Hatanaka S., Nozoe S. Chem. Lett. 1986;511-512.
17. Monnier, J. R.; Muehlbauer, P. T. US Patent 4897498, 1990 Phillips, G. W.; Falling, S. N.; Godleski, S. A.; Monnier, J. R. US Patent 5315019, 1994 Nolen, T. R.; Falling, S. N.; Hitch, D. M.; Miller, J. L.; Terrill. D. L. US Patent 5681969, 1997 Liang, S.; Price, T. W. US Patent 5633410, 1997.
18. Boaz N.W., Debenham S.D., Mackenzie E.B., Large S.E. Org. Lett. 4:2002;2421-2424.
19. Schmidt U., Lieberknecht A., Wild J. Synthesis. 1984;53-60.
20. Schmidt U., Griesser H., Leitenberger V., Lieberknecht A., Mangold R., Meyer R., Riedl B. Synthesis. 1992;487-490.
21. Carter H.E. Adams R., Bachman W.E., Fieser L.F., Johnson J.R., Snyder H.R. Organic Reactions. 3:1946;198-239 John Wiley and Sons, New York.
22. Ref. 9, p. 206.
23. Burk M.J., Allen J.G. J. Org. Chem. 62:1997;7054-7057.
24. Flynn D.L., Zelle R.E., Grieco P.A. J. Org. Chem. 48:1983;2424-2426.
25. Grehn L., Gunnarsson K., Ragnarsson U. J. Chem. Soc., Chem. Commun. 1985;1317.