Kinetic resolution of mono-and bicyclic Diels-Alder adducts via sharpless asymmetric dihydroxylation

Tetrahedron

Volumn 52, Issue 23, 1996, Pages 7901-7912

  Bakkeren, Frank J A D ^a   Klunder, Antonius J H ^a   Zwanenburg, Binne ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BETULACEAE;

2 CYCLOHEXENONE; ALKENE;

ARTICLE; CHIRALITY; DNA ADDUCT; DRUG SYNTHESIS; ENZYME KINETICS; ENZYME MECHANISM; HYDROXYLATION; NONHUMAN; OPTICAL RESOLUTION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0030043711     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00361-4     Document Type: Article

References (49)

1. (a) Helmchen, G.; Goeke, A.; Kreisz, S.; Krotz, A.; Lauer, G.H.; Linz, G. Cyclopentanoid Natural Products via Asymmetric Diels-Alder Reactions. In Studies in Natural Products Chemistry, Vol. 8. Elsevier Science Publishers B.V.: Amsterdam, 1991; 139.
2. (b) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev., 1993, 93, 741.
3. (c) Fringuelli, F.; Tatichi, A. Dienes in the Diels-Alder Reaction. Wiley: New York, 1990.
4. (d) Desimo, G.; Tacconi, G.; Barco, A.; Pollini, G.P. Natural Products Synthesis through Pericyclic Reactions. In ACS Monograph Series, No. 180, 1983.
5. (a) Paquette, L.A. Asymmetric Synthesis, Vol. 3; Morrison J.D. Ed.; Academic Press: Orlando, 1984, Chapter 7.
6. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl., 1984, 23, 876.
7. (c) Trost, B.M.; O'Krongly, D.; Belletire, J.L. J. Am. Chem. Soc., 1980, 102, 7595.
8. (d) Corey, E.J.; Ensley, H.E. J. Am. Chem. Soc., 1975, 97, 6908.
9. (e) Kagan, H.B.; Riant, O. Chem. Rev., 1992, 92, 1007.
10. (f) Lohray, B.B.; Bhushan, V. Angew. Chem., 1992, 104, 740.
11. (g) Deloux, L.; Srebnik, M. Chem. Rev., 1993, 93, 673.
12. Van Gastel, F.J.C.; Klunder, A.J.H.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas, 1991, 110, 175.
13. Sharpless, K.B.; Amberg, W.; Bennani, Y.L.; Crispino, G.A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem., 1992, 57, 2768 and references cited therein.
14. For recent reviews on asymmetric dihydroxylation reaction, see: (a) Lohray, B.B. Tetrahedron: Asymm., 1992, 3, 1317.
15. (b) Johnson, R.A.; Sharpless, K.B. Catalytic Asymmetric Dihydroxylation. In Catalytic Asymmetric Synthesis ; Ojima, I. Ed.; VCH Publishers: New York, 1993; 227.
16. (c) Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Chem. Rev., 1994, 94, 2483.
17. (d) Balavoine, G.G.A.; Manoury, E. Appl. Organomet. Chem., 1995, 9, 199.
18. (a) Classon, B.; Liu, Z.; Samuelsson, B. J. Org. Chem., 1988, 53, 6126.
19. (b) Liu, Z.; Classon, B.; Samuelsson, B. J. Org. Chem., 1990, 55, 4273.
20. (a) Sharpless, K.B.; Amberg, W.; Beller, M.; Chen, H.; Hartung, J.; Kawanami, Y.; Lübben, D.; Manoury, E.; Ogino, Y.; Shibata, T.; Ukita, T. J. Org. Chem., 1991, 56, 4585.
21. (b) Morikawa, K.; Park, J.; Andersson, P.G.; Hashiyama, T.; Sharpless, K.B. J. Am. Chem. Soc., 1993, 115, 8463.
22. (c) Crispino, G.A.; Makita, A.; Wang, Z.-M.; Sharpless, K.B. Tetrahedron Lett., 1994, 35, 543.
23. (a) Jeong, K.-S.; Sjö, P.; Sharpless, K.B. ibid., 1992, 33, 3833.
24. (b) Soderquist, J.A.; Rane, A.M.; López, C.J. ibid., 1993, 34, 1893.
25. (c) VanNieuwenhze, M.S.; Sharpless, K.B. ibid., 1994, 35, 843.
26. (d) Ko, S.Y.; Malik, M.; Dickinson, A.F. J. Org. Chem., 1994, 59, 2570.
27. Wang, L.; Sharpless, K.B. J. Am. Chem. Soc., 1992, 114, 7568.
28. While this research was in progress Wang et al. published on the asymmetric dihydroxylation of a series of conjugated cyclic cis-disubstituted olefins that gave only moderate results with a few exceptions. Wang, Z.-M.; Kakiuchi, K.; Sharpless, K.B. J. Org. Chem., 1994, 59, 6895.
29. (a) Fuji, K.; Tanaka, K.; Miyamoto, H. Tetrahedron Lett., 1992, 33, 4021.
30. (b) Hanessian, S.; Meffre, P.; Girard, M.; Beaudoin, S.; Sancéau, J.-Y.; Bennani, Y. J. Org. Chem., 1993, 58, 1991.
31. Takano, S.; Yoshimitsu, T.; Ogasawara, K. ibid., 1994, 59, 54.
32. The ligand DHQD-IND is not commercially available. The synthesis of DHQD-IND was performed as described in the supplementary material of Ref. 9.
33. (a) Koch, H. Mh. Chem., 1962, 93, 1343.
34. (b) Inukai, T.; Kasai, M. J. Org. Chem., 1965, 30, 3567.
35. (c) Devine, P.N.; Oh, T. J. Org. Chem., 1992, 57, 396.
36. 4 and concentrated in vacuo.
37. (a) Ver Nooy, C.D.; Rondestvedt Jr., C.S. J. Am. Chem. Soc., 1955, 77, 3583.
38. (b) Van Tamelen, E.E.; Shamma, M. ibid., 1954, 76, 2315.
39. (a) Varech, D.; Jacques, J. Tetrahedron, 1972, 28, 5671.
40. (b) Nakazaki, M.; Naemura, K.; Kondo, Y. J. Org. Chem., 1979, 44, 16.
41. (c) Cervinka, O.; Kriz, O. Collection Czechoslov. Chem. Commun., 1968, 33, 2342.
42. (d) Berson, J.A.; Remanick, A.; Suzuki, S.; Reynolds-Warnhoff, P.; Willner, D. J. Am. Chem. Soc., 1961, 83, 3986.
43. Kagan, H.B.; Fiaud, J.C. Top. Stereochem., 1988, 18, 249.
44. (a) Lohray, B.B.; Bhushan, V. Tetrahedron Lett., 1993, 34, 3911.
45. (b) VanNieuwenhze, M.S.; Sharpless, K.B. J. Am. Chem. Soc., 1993, 115, 7864.
46. (c) Ward, R.A.; Procter, G. Tetrahedron Lett., 1992, 33, 3363.
47. (d) Crispino, G.A.; Makita, A.; Wang, Z.-M.; Sharpless, K.B. Tetrahedron Lett., 1994, 35, 543.
48. Hawkins, J.M.; Meyer, A. Science, 1993, 260, 1918.
49. Bazbouz, A.; Christol, H.; Coste, J.; Plénat, F. Bull. Soc. Chim. Fr., 1978, II, 305-311.