Formation of optically active chromanes by catalytic asymmetric tandem oxa-Michael addition-Friedel-crafts alkylation reactions

Organic and Biomolecular Chemistry

Volumn 1, Issue 11, 2003, Pages 1953-1958

  Van Lingen, Hester L ^a,b   Zhuang, Wei ^a   Hansen, Tore ^a   Rutjes, Floris P J T ^b   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CATALYST SELECTIVITY; FRIEDEL-CRAFTS REACTION; MOLECULAR STRUCTURE; OPTICAL MATERIALS; ORGANIC COMPOUNDS;

BISOXAZOLINE; FUNCTIONALIZED CHROMANES; OPTICALLY ACTIVE CHROMANES;

ALKYLATION;

EID: 0038603070     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b303353h     Document Type: Article

References (51)

1. For reviews of tandem reactions, see e.g.: (a) G. H. Posner, Chem. Rev. 1986, 86, 831-844
2. (b) T.-L- Ho, in Tandem Organic Reactions, Wiley-Interscience, New York, 1992
3. (c) L. F. Tietze and U. Biefuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131-163
4. (d) R. A. Bunce, Tetrahedron, 1995, 48, 13103-13159
5. (e) L. F. Tietze, Chem. Rev., 1996, 96, 115-136.
6. (a) W. S. Browers, T. Ohta, J. S. Cleere and P. A. Marsella, Science, 1976, 193,542-547
7. (b) E. E. Schweizer and O. Meeder-Nycz, in Chromenes, Chromanes, Chromones, ed. G. P. Ellis, Wiley-Interscience, New York, 1977, pp. 11-139
8. (c) G. P. Ellis, I. M. Lockhart, in Chromans and Tocopherols, ed. Wiley-Interscience, New York, 1981
9. (d) G. Broggini, F. Folcio, N. Sardone, M. Sonzogni and G. Zecchi, Tetrahedron: Asymmetry, 1996, 7, 797-806 and references therein.
10. G. W. Burton and K. U. Ingold, Acc. Chem. Res., 1986, 19, 194-201 and references therein.
11. R. Hiessböck, C. Wolf, E. Richter, M. Hitzler, P. Chiba, M. Kratzel and G. Ecker, J. Med. Chem., 1999, 42, 1921-1926.
12. N. Cohen, G. Weber, B. L. Banner, R. J. Lopresti, B. Schaer, A. Focella, G. B. Zenchoff, A. Chiu, L. Todaro, M. O'Donnell, A.F. Welton, D. Brown, R. Garippa, H. Crowley and D.W. Morgan, J. Med. Chem., 1989, 32, 1842-1860.
13. C. A. Lipinski, C. E. Aldinger, T. A. Beyer, J. Bordner, D. F. Burdi, D. L. Bussolotti, P. B. Inskeep and T. W. Siegel, J. Med. Chem., 1992, 35, 2169-2177.
14. (a) M. Iyer and G. R. Tivedi, Synth. Commun., 1990, 20, 1347-1351.
15. (b) P. Wipf and W. S. J. Weiner, J. Org. Chem., 1999, 64, 5321-5324.
16. (c) Q. Wang and M. G. Finn, Org. Lett., 2000, 2, 4063-4065
17. (d) B. A. Chaudes, C. C. Lopes, R. S. C. Lopes, A. J. M. da Silva and V. Snieckus, Synthesis, 1998, 279-282
18. (e) K. A. Parker and T. L. Mindt, Org. Lett., 2001, 3, 3875-3878.
19. (a) T. Ishikawa, Y. Oku, T. Takana and T. Kumamoto, Tetrahedron Lett., 1999, 40, 3777-3780
20. (b) T. Tanaka, T. Kumamoto and T. Ishikawa, Tetrahedron: Asymmetry, 2000, 11, 4633-4637
21. (c) T. Tanaka, T. Kumamoto and T. Ishikawa, Tetrahedron Lett., 2000, 41, 10229-10232.
22. 2-bisoxazoline Lewis acid catalysts, see e.g.: (a) A. Pfaltz, Acc. Chem. Res., 1993, 26, 339-345
23. (b) A. K. Ghosh, P. Mathivanen and J. Cappiello, Tetrahedron: Asymmetry, 1998, 9, 1-45
24. (c) K. A. Jørgensen, M. Johannsen, S. Yao, H. Audrain and J. Thorhauge, Acc. Chem. Res., 1999, 32, 605-613
25. (d) J. S. Johnson and D. A. Evans, Acc. Chem. Res., 2000, 33, 325-335.
26. (a) S. Kanemasa, Y. Oderatoshi and E. Wada, J. Am. Chem. Soc., 1999, 121, 8675-8676
27. (b) W. Zhuang, R. G. Hazell and K. A. Jørgensen, Chem. Commun., 2001, 1240-1241
28. (c) P. D. A. Evans, K. A. Scheidt, J. N. Johnston and M. C. Willis, J. Am. Chem. Soc., 2001, 123, 4480-4491
29. (d) G. Desimoni, G. Faita, S. Filippone, M. Mella, M. G. Zampori and M. Zema, Tetrahedron, 2001, 57, 10203-10212
30. J. Zhou and Y. Tang, J. Am. Chem. Soc., 2002, 124, 9030-9031
31. (f) M. P. Sibi and J. X. Chen, Org. Lett., 2002, 4, 2933-2936.
32. (a) N. Gathergood, W. Zhuang and K. A. Jørgensen, J. Am. Chem. Soc., 2000, 122, 12517-12522
33. (b) W. Zhuang, N. Gathergood, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2001, 66, 1009-1013
34. (c) K. B. Jensen, J. Thorhauge, R. G. Hazell and K. A. Jørgensen, Angew. Chem., Int. Ed., 2001, 40, 160-163
35. (d) W. Zhuang, T. Hansen and K. A. Jørgensen, Chem. Commun., 2001, 347-348.
36. Recently, two groups independently reported the use of bisoxazoline ligands in a tandem reaction: (a) S. Kaden and M. Hiersemann, Synlett, 2002, 12, 1999-2002
37. (b) E. Wada, H. Koga and G. Kumaran, Tetrahedron Lett., 2002, 43, 9397-9400.
38. H. L. van Lingen, J. K. W. van der Mortel, K. F. W. Hekking, F. L. van Delft, T. Sonke and F. P. J. T. Rutjes, Eur. J. Org. Chem., 2003, 19, 317-324.
39. Box-ligand 4d was obtained by dimethylation of the bridging methylene group from the commercially available analogue, according to: S. E. Denmark and C. M. Stiff, J. Org. Chem., 2000, 65, 5875-5878.
40. The first synthesis of this ligand was described by: G. Desimoni, G. Faita and M. Mella, Tetrahedron, 1996, 52, 13649-13654.
41. For recent entries into the use of the DBFOX/Ph ligand, see e.g.: Kanemasa, Y. Oderaotoshi, S.-I. Sakagushi, H. Yamamoto, J. Tanaka, E. Wada and D. P. Curran, J. Am. Chem. Soc., 1998, 120, 3074-3088.
42. For a recent review concernng the use of BINOL as a ligand, see e.g.: T. Katsuki, Curr. Org. Chem., 2001, 5, 663-678.
43. For a recent review concerning the use of salen-type ligands, see e.g.: C. Rosini, L. Frazini, A. Raffaelli and P. Salvadori, Synthesis, 1992, 503-517.
44. K. V. Gothelf, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1996, 61, 346-355.
45. (a) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf and K. A. Jørgensen, Angew. Chem., Int. Ed., 2001, 40, 2995-2997
46. (b) C. Christensen, K. Juhl, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2002, 67, 4875-4881.
47. 3N affording racemic chromane 1a in 23% yield and side product 6a in 31% yield.
48. J. Thorhauge, M. Roberson, R. G. Hazell and K. A. Jørgensen, Chem. Eur. J., 2002, 8, 1888-1898.
49. -1; 30861 reflections were measured, giving 7316 independent, of which 6592 with I > 3σ(I) were used in the refinements. The internal agreement had R = 0.087, the final R = 0.028, Rw = 0.035, GOF = 1.21, for the significant reflections.
50. ∞1; 24177 reflections were measured, giving 7639 independent, of which 5147 with I > 3σ(I) were used in the refinements. The internal agreement had R = 0.079, the final R = 0.033, Rw = 0.035, GOF = 0.90, for the significant reflections.
51. Optimisations were performed using Spartan (version 5.1.3), Counterions and solvent were omitted during calculations.