Synthesis of Enantiomerically Pure Binaphthyl Derivatives. Mechanism of the Enantioselective, Oxidative Coupling of Naphthols and Designing a Catalytic Cycle

Journal of Organic Chemistry

Volumn 58, Issue 17, 1993, Pages 4534-4538

  Smrčina, Martin ^a   Poláková, Jana ^a   Vyskočil, Štěpán ^a   Kočovský, Pavel ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751385309     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00069a010     Document Type: Article

References (52)

1. For reviews, see, e.g.: Morrison, J. D. Asymmetric Synthesis; Academic: New York, 1983–1985; Vols. 1–5.
2. Kočovský, P.; Tureček, F.; Hájíček, J. Synthesis of Natural Products: Problems of Regioselectivity; CRC: Boca Raton, FL, 1986; Vols. I and II.
3. Jacques, J.; Fouquey, C. Org. Synth. 1988, 67, 2.
4. Narasaka, K. Synthesis 1991, 1.
5. Trost, B. M. Pure Appl. Chem. 1992, 64, 315.
6. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
7. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255.
8. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
9. Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264 and references cited therein.
10. Parker, D. Chem. Rev. 1991, 91, 1441.
11. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
12. Takaya, H.; Ohta, T.; Mashima, K.; Noyori, R. Pure Appl. Chem. 1990, 62, 1135.
13. Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421.
14. Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
15. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807.
16. Blaser, H.-U. Chem. Rev. 1992, 92, 935.
17. Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051.
18. Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179.
19. For a review, see: Rosmi, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503.
20. Stará, I.; Starý, I.; Závada, J. Tetrahedron: Asymmetry 1992, 3, 1365.
21. Stará, I.; Starý, I.; Závada, J. J. Org. Chem. 1992, 57, 6966.
22. Chong, J. M.; MacDonald, G. K.; Park, S. B.; Wilkinson, S. H. J. Org. Chem. 1993, 58, 1266.
23. Kazlauskas, R. J. J. Am. Chem. Soc. 1989, 111, 4953 and references
24. Feringa, B.; Wynberg, H. Bioorg. Chem. 1978, 7, 397.
25. Yamamoto, K.; Fukushima, H.; Nakazaki, M. J. Chem. Soc., Chem. Commun. 1984, 1490.
26. Brussee, J.; Groenendijk, J. L. G.; te Koppele, J. M.; Jansen, A. C. A. Tetrahedron 1985, 41, 3313.
27. Yamamoto, K.; Yumioka, H.; Okamoto, Y.; Chikamatsu, H. J. Chem. Soc., Chem. Commun. 1987, 168.
28. Smrčina, M.; Lorenc, M.; Hanuš, V.; Sedmera, P.; Kočovský, P. J. Org. Chem. 1992, 57, 1917.
29. Smrčina, M.; Lorenc, M.; Hanuš, V.; Kočovský, P. Synlett 1991, 231.
30. Toda, F.; Tanaka, K.; Iwata, S. J. Org. Chem. 1989, 54, 3007 and references cited therein.
31. Yamamoto, H.; Fukushima, H.; Okamoto, Y.; Hatada, K.; Nakazaki, M. J. Chem. Soc., Chem. Commun. 1984, 1111.
32. Diederich F.; Hester, M. R.; Uyeki, M. A. Angew. Chem., Int. Ed. Engl. 1988, 27, 1705.
33. Hovorka, M.; Günterová, J.; Závada, J. TetrahedronLett. 1990, 31, 413.
34. Hovorka, M.; Závada, J. Org. Prep. Proc. Int. 1991, 23, 200.
35. Hovorka, M.; Ščgel, R.; Günterová, J.; Tichý, M.; Závada, J. Tetrahedron 1992, 48, 9503.
36. Hovorka, M.; Závada, J. Tetrahedron 1992, 48, 9517.
37. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates, and Resolutions; J. Wiley: New York, 1981.
38. For examples of efficient catalytic oxidation cycles, see, e.g.: Bäckvall, J.-E. Acc. Chem. Res. 1983, 16, 335.
39. McMurry, J. E.; Kočovský, P. Tetrahedron Lett. 1984, 25, 4187.
40. Hanson, S.; Heuman, A.; Rein, T.; Akermark, B. J. Org. Chem. 1990, 55, 975.
41. Byström, S. E.; Larsson, E. M.; Akermark, B. J. Org. Chem. 1990, 55, 5674.
42. Bäckvall, J.-E.; Awasthi, A. K.; Renko, Z. D. J. Am. Chem. Soc. 1987, 109, 4750.
43. Bäckvall, J.-E.; Hopkins, R. B.; Grennberg, H.; Mader, M.; Awasthi, A. K. J. Am. Chem. Soc. 1990, 112, 5160.
44. Bäckvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473.
45. Chowdhury, R. L.; Bäckvall, J.-E. J. Chem. Soc., Chem. Commun. 1991, 1063.
46. Wang, G.-Z.; Bäckvall, J.-E. J. Chem. Soc., Chem. Commun. 1992, 337.
47. D −34° (c 1.0, THF): Kyba, E. P.; Gokel, G. W.; de Jong, F.; Koga, K.; Sousa, L. R.; Siegel, M. G.; Kaplan, L.; Sogah, G. D. Y.; Cram, D. J. J. Org. Chem. 1977, 42, 4173.
48. In AT-2, the less stable diastereoisomer (i.e., less well stabilized by solvation) which, naturally, is less populated in the solution crystallizes preferentially to reach more stabilkation in the crystalline lattice. Continuous equilibrium in the solution may finally produce a diastereoisomerically pure crystalline material in high yield. By contrast, AT-1 affords a mixture which reflects the thermodynamic equilibrium in the solution, which is not perturbed by crystallization. Hence, AT-2 results in the preferential formation of the less stable (in solution) diastereoisomer (van&t Hoff-Dimroth rule). For discussion, see, e.g.: Buchanan, C.; Graham, S. H. J. Chem. Soc. 1950, 500.
49. 4 The absolute configuration was determined by Yamada: Akimoto, H.; Shioiri, T.; Iitaka, Y.; Yamada, S. J. Tetrahedron Lett. 1968, 97.
50. Akimoto, H.; Yamada, S. Tetrahedron 1971, 27, 5999.
51. Hayashi, T.; Hayashizuka, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153.
52. Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732.