Catalytic Asymmetric Epoxidations with Chiral Iron Porphyrins

Journal of the American Chemical Society

Volumn 105, Issue 18, 1983, Pages 5791-5796

  Groves, John T ^a   Myers, Richard S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845550903     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00356a016     Document Type: Article

References (27)

1. Morrison, J. D.; Mosher, H. S. “Asymmetric Organic Reactions” Prentice-Hall: Englewood Cliffs, NJ, 1971; p. 160. (b) Caplar, V.; Comisso, G.; Sunjic, V. Synthesis 1981, 85-116.
2. Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D.; Weinkaufff, D. J. J. Am. Chem. Soc. 1975, 97, 2567-68. (b) U.S. Patent 4008 281, 1975 (Monsanto).
3. Pirkle, W. H.; Rinaldi, P.L. J. Org. Chem. 1977, 42, 2080-82.
4. Kagan, H. B., Mimoun, H.; Mark, C.; Schurig, V. Angew. Chem., Int. Ed. Engl. 1979, 18, 485-86.
5. Helder, R.; Hummelen, J. C.; Laane, R. W. P. M.; Wiering, J. S.; Wynberg, H. Tetrahedron Lett. 1976, 1831-34.
6. Michaelson, R. C.; Palermo, R. E.; Sharpless, K.B. J. Am. Chem. Soc. 1977, 99, 1990-92.
7. Yamada, S.; Mashiko, T.; Terashima, S. J. Am. Chem. Soc. 1977, 99, 1988-90.
8. Katsuki, T.; Sharpless, K.B. J. Am. Chem. Soc. 1980, 102, 5974-76. (b) Rossiter, B. E.; Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 464-65.
9. Tani, K.; Hanafusa, M.; Otsuka, S. Tetrahedron Lett. 1979, 3017-20.
10. Ohta, H.; Tetsukawa, H. J. Chem. Soc., Chem. Commun. 1978, 849-50.
11. May, S. W.; Schwartz, R.D. J. Am. Chem. Soc. 1974, 96, 4031-32.
12. Groves, J. T.; Nemo, T. E.; Myers, R.S. J. Am. Chem. Soc. 1979, 101, 1032. (b) Groves, J. T.; Kruper, W. J.; Nemo, T. E.; Myers, R. S. J. Mol. Catal. 1980, 7, 169-177.
13. Chang, C. K.; Kuo, M.-J. J. Am. Chem. Soc. 1979, 101, 3413-5.
14. Collman, J. P.; Gagne, R. R.; Reed, C. A.; Halbert, T. R.; Lang, G.; Robinson, W.T. J. Am. Chem. Soc. 1975, 97, 1427-39.
15. Pettersson, K. Ark. Kemi. 1957, 10, 283-96.
16. Storm, C. B.; Teklu, Y. J. Am. Chem. Soc. 1972, 94, 1745-47.
17. Yoon, N. M.; Brown, H.C. J. Am. Chem. Soc. 1968, 90, 2927-38.
18. Groves, J. T.; Nemo, T. E. J. Am. Chem. Soc., in press.
19. Groves, J. T.; Haushalter, R. C.; Nakamura, M.; Nemo, T. E.; Evans, B. J. J. Am. Chem. Soc. 1981, 103, 2884-86. (b) Nakamura, M., unpublished results.
20. For a review of the concepts of host-guest interactions see: (a) Cram, D. J.; Cram, J. M. Acc. Chem. Res. 1978, 11, 8-14. (b) Cram, D. J. In “Applications of Biochemical Systems in Organic Chemistry” pp. 815-873.
21. Mislow, K.; Graseman, P.A. J. Org. Chem. 1958, 23, 2027-29.
22. Hall, D. M.; Turner, E.E. J. Chem. Soc. 1955, 1242-51.
23. Buchler, J. W.; Lay, K.L.Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1975, 30B, 385-92.
24. Lindsay-Smith, J. R.; Shaw, B. A. J.; Jeffrey, A. M.; Jerina, D.M. J. Chem. Soc., Perkin Trans. 2 1977, 1583-89.
25. Winter, G. Inorg. Synth. 1973, 14, 101-4.
26. Moretti, I.; Torre, G. Tetrahedron Lett. 1969, 8, 2717-20.
27. Reilly, C. A.; Swalen, J.D. J. Chem. Phys. 1960, 32, 1378-85.