From central to planar chirality, the first example of atropenantioselective cycloetherification

Organic and Biomolecular Chemistry

Volumn 1, Issue 1, 2003, Pages 30-32

  Islas Gonzalez, Gabriela ^a   Bois Choussy, Michèle ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SALTS; SOLVENTS; STOICHIOMETRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TEMPERATURE;

AMMONIUM HYDROXIDE; ATROPENANTIOSELECTIVE CYCLOETHERIFICATION; CYCLIZATION; INTRAMOLECULAR NUCLEOPHILIC AROMATIC SUBSTITUTION; LINEAR ACHIRAL DIARYLHEPTANOID; TETRABUTYLAMMONIUM FLUORIDE;

AMMONIUM COMPOUNDS;

EID: 0042324377     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b208905j     Document Type: Article

References (31)

1. K. E. Malterud, T. Anthonsen and J. Hjortas, Tetrahedron Lett., 1976, 3069-3072.
2. M. Toyota, T. Yoshida, Y. Kan, S. Takaoka and Y. Asakawa, Tetrahedron Lett., 1996, 37, 4745-4748.
3. R. Noyori, Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, Inc., New York, 1994.
4. P. J. Pye, K. Rossen, R. A. Reamer, N. N. Tsou, R. P. Volante and P. J. Reider, J. Am. Chem. Soc., 1997, 119, 6207-6208.
5. (a) T. Hayashi, K. Hayashizaki, T. Kiyoi and Y. Ito, J. Am. Chem. Soc., 1988, 110, 8153-8156
6. (b) T. Hayashi, S. Nizuma, T. Kamikawa, N. Suzuki and Y. Uozumi, J. Am. Chem. Soc., 1995, 117, 9101-9102
7. (c) T. Kamikawa and T. Hayashi, Tetrahedron, 1999, 55, 3455-3466.
8. (a) A. N. Cammidge and K. V. L. Crépy, Chem. Commun., 2000, 1723-1724
9. (b) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2000, 122, 12051-12052.
10. (a) For recent reviews on enantioselective synthesis and application of planar chiral (arene)chromium complexes and ferrocene derivatives, see: K. Kamikawa and M. Uemura, Synlett, 2000, 938-949
11. (b) C. Bolm and K. Muñiz, Chem. Soc. Rev., 1999, 28, 51-59
12. (c) C. J. Richards and A. J. Locke, Tetrahedron: Asymmetry 1998, 9, 2377-2407
13. (d) A. Togni, Angew. Chem., Int. Ed. Engl., 1996, 35, 1475-1477.
14. J. Zhu, Synlett, 1997, 133-144.
15. (a) K. Burgess, D. Lim and C. I. Martinez, Angew. Chem. Int. Ed. Engl., 1996, 35, 1077-1078
16. (b) K. C. Nicolaou, C. N. C. Boddy, S. Bräse and N. Winssinger, Angew. Chem., Int. Ed., 1999, 38, 2096-2152
17. (c) J. S. Sawyer, Tetrahedron, 2000, 56, 5045-5065.
18. T. Temal-Laïb, J. Chastanet and J. Zhu, J. Am. Chem. Soc., 2002, 124, 583-590.
19. (a) M. Bois-Choussy, L. Neuville, R. Beugelmans and J. Zhu, J. Org. Chem., 61, 9309-9322
20. (b) R. Beugelmans, M. Bois-Choussy, C. Vergne, J. P. Bouillon and J. Zhu, Chem. Commun., 1996, 1029-1030
21. (c) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow and J. L. Katz, Angew. Chem. Int. Ed., 1998, 37, 2700-2704
22. (d) D. A. Evans, C. J. Dinsmore, P. S. Watson, M. R. Wood, T. I. Richardson, B. W. Trotter and J. L. Katz, Angew. Chem. Int. Ed., 1998, 37, 2704-2708.
23. K. C. Nicolaou and C. N. C. Boddy, J. Am. Chem. Soc., 2002, 124, 10451-10455.
24. G. Islas-Gonzalez and J. Zhu, J. Org. Chem., 1999, 64, 914-924.
25. Compound 7 was prepared from cinchonine in two steps: a) BnBr, acetone, reflux, 72h. b) Amberlyst A-26, MeOH. Treatment of compound 7 in MeOH with HF (1 M) gave 8 in quantitative yield. Cinchonidine derivative 10 was prepared in a similar fashion.
26. (a) B. Lygo and P. G. Wainwright, Tetrahedron Lett., 1997, 38, 8595-8598
27. (b) E. J. Corey, F. Xu and M. C. Noe, J. Am. Chem. Soc., 1997, 119, 12414-12415.
28. 2, 0 °C to room temperature, 2 h.
29. A. Loupy, B. Tchoubar and D. Astruc, Chem. Rev., 1992, 92, 1141-1165.
30. D. Hoppe and T. Hense, Angew. Chem. Int. Ed. Engl., 1997, 36, 2282-2316.
31. G. Islas-Gonzalez and J. Zhu, Synlett, 2000, 412-414.