A study of the stereodirecting effect by an allylic nitrogen substituent on dihydroxylation reactions of cyclic double bonds[1]

Journal of Industrial and Engineering Chemistry

Volumn 3, Issue 4, 1997, Pages 326-334

  Oh, Joon Seok ^a   Hong, Yoo Seong ^a   Kim, Young Gyu ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2042464342     PISSN: 1226086X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (49)

1. (a) Excerpted in part from the M. E. thesis of Y. S. Hong, Seoul National University, Feb. 1997.
2. (b) Presented in part at the Fall '97 Conference of the Korean Society of Industrial and Engineering Chemistry, The University of Suwon, Hwasung- Gun, Kyonggi-Do, October Si-November 1, 1997: No. 1PB-29
3. (a) F. M. Hauser and S. R. Ellenberger, Chem. Rev. 86, 35 (1986).
4. (b) G. J. Thomas, Synthesis of Anthracyclines Related to Daunomycin in Recent Progress in the Chemical Synthesis of Antibiotics, G. Lukacs and M. Ohno (eds.), p. 467, Springer- Verlag, Berlin (1990).
5. M. P. Sibi, J. Lu and J. Edwards, /. Org. Chem., 62, 5864 (1997) and references therein.
6. (a) T. Yokomatsu, Y. Yuasa, and S. Shibuya, Heterocycles, 33, 1051 (1992).
7. (b) G. Cardillo and C. Tomasini, Chem. Soc. Rev., 25, 117 (1996).
8. G. Veeresha and A. Datta, Tetrahedron Lett., 38, 5223 (1997) and references therein.
9. (a) K. C. Nicolaou, W.-N. Dai, and R. K. Guy, Angew. Chem., Int. Ed. Engl. 33, 15 (1994).
10. (b) M. Hepperle and G. I. Georg, Drugs Fut. 19, 573 (1994).
11. C. Gennari, M. Carcano, M. Donghi, N. Mongelli, E. Vanotti, and A. Vulpetti, /. Org. Chem., 62, 4746 (1997) and references therein.
12. For rather recent references, see inter alia:
13. (a) R. Wild and R. R. Schmidt, Tetrahedron: Asymmetry, 5, 2195 (1994).
14. (b) Y.-L. Li, X.-H. Mao, and Y.-L. Wu, /. Chem. Soc., Perkin Trans, l, 1559 (1995).
15. M. Shimizu, I. Wakioka, and T. Fujisawa, Tetrahedron Lett., 38, 6027 (1997).
16. (a) G. M. Coppola and H. F. Schuster, Asymmetric Synthesis: Construction of Chiral Molecules using Amino Acids, Wiley, New York, 1987.
17. (b) R M. Williams, Synthesis of Optically Active aAmino Acids, Pergamon, Oxford, 1989.
18. (a) B. E. Maryanoff and A. B. Reitz, Chem. Rev., 89, 863 (1989).
19. (b) E. Vedejs and M. J. Peterson, Top. Stereochem., 21, 1 (1994).
20. (a) J. K. Cha, W. J. Christ, and Y. Kishi, Tetrahedron, 40, 2247 (1984).
21. (b) }. K. Cha and N.-S. Kirn, Chem. Rev. 95, 1761 (1995).
22. H. C. Kolb, M. S. VanNieuwenhze, and K. B. Sharpless, Chem. Rev. 94, 2483 (1994).
23. R. W. Hoffman, Chem. Rev. 89, 89 (1989).
24. (e) A. H. Hoveyda, D. A. Evans, and G. C. Fu, Chem. Rev. 93, 1307 (1993)
25. (a) T. J. Donohoe, R. Garg, and P. R. Moore, Tetrahedron Lett., 37, 3407 (1996).
26. (b) T. J. Donohoe, P. R. Moore, and R L. Beddoes, /. diem. Soc., Perkin Trans, 1, 43 (1997).
27. T. J. Donohoe, P. R. Moore, and M. J. Waring, Tetrahedron Lett., 38, 5027 (1997).
28. For references of other approaches for the vicamino alcohols, see: U. M. Lindstrm, R Franckowiak, N. Pinault, and P. Somfai, Tetrahedron Lett., 38, 2027 (1997) and references cited therein.
29. 4 and the allylic substituent.
30. There are a few reports on the solvent effect on facial stereoselectivity in olefins with allylic substituents, which reveal seemingly inconsistent results. See:
31. (a) G. Poli, Tetrahedron Lett., 30, 7385 (1989).
32. (b) M. Hirama, T. Oishi, and S. Ito, /. Chem. Soc., Chem. Commun., 665 (1989).
33. M. Burdisso, R. Gandolfi, and A. Rastelli, Tetrahedron Lett., 32, 2659 (1991).
34. D. J. Krysan, T. W. Rockway, and A. R. Haight, Tetrahedron: Asymmetry, 5, 625 (1994).
35. (a) N. M. Targett, J. P. Kikoyne, and B. Green, /. Org. Chem., 44, 4962 (1979).
36. (b) S. W. Pelletier, H. P. Chokshi, and H. K. Desai, /. Nat. Prod., 49, 892 (1986).
37. J. C. Coll and B. F. Bowden, /. Nat. Prod., 49, 934 (1986).
38. J. Leonard, B. Lygo, and G. Procter, Advanced Practical Organic Chemistry 2nd ed., Chap. 11, pp. 215-216, Blackie Academic & Professional, London (1995).
39. (a) A. Koziara, K. Osowska-Parewicka, S. Zawadzki, and A. Zwierzak, Synthesis, 202 (1988). (b) H. Lehmkuhl, F. Rabet, and K. Haushild, Synthesis, 184 (1977).
40. (a) A. W. Johnson, Ylides and Imines of Phosphorus, Chap. 13, pp. 403-483, Wiley, New York (1993).
41. (b) S, I. Murahashi, Y. Taniguchi, Y. Imada, and Y. Tanigawa, /. Org. Chem., 54, 5864 (1989).
42. S. I. Murahashi, Y. Imada, and Y. Tanigawa, Y. Taniguchi, Tetrahedron Lett., 27, 227 (1986).
43. (a) V. Van Rheenen, R. C. Kelly, and D. Y. Cha, Tetrahedron Lett., 1973 (1976).
44. (b) M. Schroder Chem. Rev., 80, 187 (1980).
45. (a) A. Leo, C. Hansch, and D. Elkins, Chem. Rev., 71, 525 (1971).
46. (b) C. Laane, S. Boeren, K. Vos, and C. Veeger, Biotechnol. Bioeng., 30, 81 (1987).
47. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry 2nd. ed., Chap. 7, p. 339, VCH, Weinheim (1988).
48. M. T. Reetz, Angew. Chem., Int. Ed. Engl. 30, 1531 (1991).
49. S. Saito, Hitoshi, M. Inaba, and T. Moriwake, Tetrahedron Lett., 30, 837 (1989).