Enantioselective Synthesis of Non-Racemic Chiral Molecules on an Industrial Scale

Topics in Stereochemistry

Volumn 19, Issue , 2007, Pages 209-226

  Scott, John W ^a  

^a HOFFMANN LA ROCHE INC   (United States)

Author keywords

Amino acids; Enantioselective cyclopropanatian; Enantioselective hydroboration; Enantioselective synthesis; Epoxidation

Indexed keywords

AMINO ACIDS; ENANTIOSELECTIVITY; EPOXIDATION; STEREOCHEMISTRY;

CHIRAL MOLECULE; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; HYDROBORATION; INDUSTRIAL SCALE;

SYNTHESIS (CHEMICAL);

EID: 85050328245     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470147283.ch4     Document Type: Chapter

References (47)

1. Powell, J. R.; Ambre, J. J.; Ruo, T. I. in Wainer, I. W.; Drayer, D. E., Eds.; Drug Stereochemistry; Marcel Dekker: New York, 1988; pp 245-270.
2. Ariëns, E. J.; Soudijn, W.; Timmermans, P.B.M.W.M. Stereochemistry and Biological Activity of Drugs; Blackwell Scientific: Palo Alto, CA, 1983.
3. Brand, J. M.; Young, J. C; Silverstein, R. M. in Herz, W. E.; Grisebach, H.; Kirby, G. W., Eds; Progress in the Chemistry of Organic Natural Products; Springer-Verlag: New York, 1979; Vol. 37, pp 1-190.
4. Scott, I. W. in Scott, J. W.; Morrison, J. D., Eds.; Asymmetric Synthesis; Academic: Orlando, 1984, Vol. 4, pp 1-226.
5. Seebach, D.; Hungerbühler, E. in Scheffold, R., Ed.; Modern Synthetic Methods 1980, Otto Salle Verlag, Frankfurt am Main and Verlag Sauerländer, Aarau, 1980.
6. Nógrádi, M. Stereoselective Synthesis; VCH Verlagsgesellschaft: Weinheim, 1986, pp 313-314.
7. Coppola, G. M.; Schuster, V. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; John Wiley and Sons: New York, 1987.
8. Kaneko, T.; Izurai, Y.; Chibata, I.; Itoh, T., Eds; Synthetic Production and Utilization of Amino Acids; John Wiley and Sons: New York, 1974.
9. Berkoff, C. E.; Rivard, D. E.; Kamholz, K.; Wellman, G. R.; Winicov, H. CHEMTECH 1986, 16, 552-559.
10. Morrison, J. D., Ed.; Asymmetric Synthesis; Academic: Orlando, 1985, Vol. 5.
11. Bosnich, B.; Fryzuk, M. D. in Geoffrey, G. L., Ed.; Topics in Stereochemistry; John Wiley and Sons: New York, 1981; Vol. 12, pp 119-154.
12. Knowles, W. S. Acc. Chem. Res. 1983, 16, 106-112.
13. Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D.; Weinkauff, D. J. J. Am. Chem. Soc. 1975, 97, 2567-2569.
14. ANIC S.p.A., Eur. Patent 77 099, 1983.
15. Sharpless, K. B., Massachusetts Institute of Technology, personal communication, 1986.
16. Scott, J. W.; Keith, D. D.; Nix, Jr., G.; Parrish, D. R.; Remington, S.; Roth, G. P.; Town-send, J. M.; Valentine, Jr., D.; Yang, R. J. Org. Chem. 1981, 46, 5086-5093.
17. Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori, R. J. Am. Chem. Soc. 1987, 109, 1596-1597.
18. Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117-7119.
19. Kitamura, M.; Hsiao, Y.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 41, 4829-4832.
20. Aratani, T. Pure Appl. Chem. 1985, 57, 1839-1844.
21. Rossiter, B. E. in Morrison, J. D., Ed. Asymmetric Synthesis, Vol. 5, Academic Press, Orlando, 1985, pp. 193-246.
22. Rossiter, B. E.; Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 464-465.
23. Hill, J. G.; Sharpless, K. B.; Exon, C. M.; Regenye, R. Org. Syn. 1984, 63, 66-78.
24. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
25. Coughenour, G., ARCO Chemical Company, personal communication, 1988.
26. Ladner, W. E.; Whitesides, G. M. J. Am. Chem. Soc. 1984, 106, 7250-7251.
27. Whitesides, G., Harvard Univ., personal communication, 1987.
28. Akutagawa, S., Takasago Corporation, personal communication, 1986.
29. Tani, K. Pure Appl. Chem. 1985, 57, 1845-1854.
30. Tani, K.; Yamagata, T.; Akutagawa, S.; Kumobayashi, H.; Taketomi, T.; Takaya, H.; Miyashita, A.; Noyori, R.; Otsuka, S. J. Am. Chem. Soc. 1984, 106, 5208-5217.
31. Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168.
32. Wynberg, H.; Staring, E. G. J. J. Org. Chem. 1985, 50, 1977-1979.
33. Staring, E. G. J.; Mooriag, H.; Wynberg, H. Reel. Trav. Chim. Pays-Bas 1986, 105, 374-375.
34. New, M., Lonza Ltd., personal communication, 1988.
35. Wynberg, H., University of Groningen, personal communication, 1987.
36. Partridge, J. J.; Chadha, N. K.; Uskokovic, M. R. Org. Syn. 1984, 63, 44-56.
37. Haubenstock, H. in Allinger, N. L.; Eliel, E. L.; Wilen, S. H., Eds.; Topics in Stereochemistry; John Wiley and Sons: New York, 1983; Vol. 14, pp 231-300.
38. Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823-2824.
39. Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071-6072.
40. Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690-1691.
41. Muchow, G.; Vannoorenberghe, Y.; Buono, G. Tetrahedron Lett. 1987, 28, 6163-6166.
42. Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841-4842.
43. Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233-5236.
44. Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5237-5240.
45. Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111-7115.
46. Grandbois, E. R.; Howard, S. I.; Morrison, I. D. in Morrison, S. D. Ed.; Asymmetric Synthesis; Academic: Orlando, 1983; Vol. 2, pp 71-90.
47. DeCamp, W. H. Chirality 1989, 1, 2-6.