Enantioselective synthesis of α,β,α'-trisubstituted cyclic ethers

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9728-9738

  Mujica, M Teresa ^a   Afonso, María M ^a   Galindo, Antonio ^a   Palenzuela, J Antonio ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE;

ARTICLE; CHIRALITY; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032567409     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981188w     Document Type: Article

References (59)

1. Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
2. Faulkner, D. J. Nat. Prod. Rep. 1997, 14, 259.
3. Fukuzawa, A.; Masamune, T. Tetrahedron Lett. 1981, 22, 4081.
4. (a) Irie, T.; Suzuki, M.; Masamune, T. Tetrahedron Lett. 1965, 1091.
5. (b) Irie, T.; Suzuki, M.; Masamune, T. Tetrahedron. 1968, 24, 4193.
6. (c) Cameron, A. F.; Cheung, K. K.; Ferguson, G.; Robertson, J. M. J. Chem. Soc. B 1969, 559.
7. (d) Cameron, A. F.; Cheung, K. K.; Ferguson, G.; Robertson, J. M. J. Chem. Soc., Chem. Commun. 1965, 638.
8. (a) King, T. J.; Imre, S.; Oztunc, A.; Thomson, R. H. Tetrahedron Lett. 1979, 1453.
9. (b) Howard, B. M.; Schulte, G. R.; Fenical, W. Tetrahedron 1980, 36, 1747.
10. Recent examples: (a) Ravelo, J. L.; Regueiro, A.; Martín, J. D. Tetrahedron Lett. 1992, 33, 3389. (b) Hoffmann, R. W.; Münster, I. Tetrahedron Lett. 1995, 36, 1431. (c) Alvarez, E.; Díaz, M. T.; Hanxing, L.; Martín J. D. J. Am. Chem. Soc. 1995, 117, 1437. (d) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (e) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. (f) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611. (g) Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446. (h) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548.
11. Recent examples: (a) Ravelo, J. L.; Regueiro, A.; Martín, J. D. Tetrahedron Lett. 1992, 33, 3389. (b) Hoffmann, R. W.; Münster, I. Tetrahedron Lett. 1995, 36, 1431. (c) Alvarez, E.; Díaz, M. T.; Hanxing, L.; Martín J. D. J. Am. Chem. Soc. 1995, 117, 1437. (d) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (e) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. (f) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611. (g) Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446. (h) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548.
12. Recent examples: (a) Ravelo, J. L.; Regueiro, A.; Martín, J. D. Tetrahedron Lett. 1992, 33, 3389. (b) Hoffmann, R. W.; Münster, I. Tetrahedron Lett. 1995, 36, 1431. (c) Alvarez, E.; Díaz, M. T.; Hanxing, L.; Martín J. D. J. Am. Chem. Soc. 1995, 117, 1437. (d) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (e) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. (f) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611. (g) Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446. (h) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548.
13. Recent examples: (a) Ravelo, J. L.; Regueiro, A.; Martín, J. D. Tetrahedron Lett. 1992, 33, 3389. (b) Hoffmann, R. W.; Münster, I. Tetrahedron Lett. 1995, 36, 1431. (c) Alvarez, E.; Díaz, M. T.; Hanxing, L.; Martín J. D. J. Am. Chem. Soc. 1995, 117, 1437. (d) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (e) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. (f) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611. (g) Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446. (h) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548.
14. Recent examples: (a) Ravelo, J. L.; Regueiro, A.; Martín, J. D. Tetrahedron Lett. 1992, 33, 3389. (b) Hoffmann, R. W.; Münster, I. Tetrahedron Lett. 1995, 36, 1431. (c) Alvarez, E.; Díaz, M. T.; Hanxing, L.; Martín J. D. J. Am. Chem. Soc. 1995, 117, 1437. (d) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (e) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. (f) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611. (g) Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446. (h) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548.
15. Recent examples: (a) Ravelo, J. L.; Regueiro, A.; Martín, J. D. Tetrahedron Lett. 1992, 33, 3389. (b) Hoffmann, R. W.; Münster, I. Tetrahedron Lett. 1995, 36, 1431. (c) Alvarez, E.; Díaz, M. T.; Hanxing, L.; Martín J. D. J. Am. Chem. Soc. 1995, 117, 1437. (d) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (e) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. (f) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611. (g) Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446. (h) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548.
16. Recent examples: (a) Ravelo, J. L.; Regueiro, A.; Martín, J. D. Tetrahedron Lett. 1992, 33, 3389. (b) Hoffmann, R. W.; Münster, I. Tetrahedron Lett. 1995, 36, 1431. (c) Alvarez, E.; Díaz, M. T.; Hanxing, L.; Martín J. D. J. Am. Chem. Soc. 1995, 117, 1437. (d) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (e) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. (f) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611. (g) Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446. (h) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548.
17. Recent examples: (a) Ravelo, J. L.; Regueiro, A.; Martín, J. D. Tetrahedron Lett. 1992, 33, 3389. (b) Hoffmann, R. W.; Münster, I. Tetrahedron Lett. 1995, 36, 1431. (c) Alvarez, E.; Díaz, M. T.; Hanxing, L.; Martín J. D. J. Am. Chem. Soc. 1995, 117, 1437. (d) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (e) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127. (f) Inoue, M.; Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1997, 38, 1611. (g) Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446. (h) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548.
18. (a) Nicolaou, K. C.; Prasad, C. V. C.; Hwang, C.-K.; Duggan, M. E.; Veale, C. A. J. Am. Chem. Soc. 1989, 111, 5321.
19. (b) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
20. (c) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5335.
21. (d) Cooper, A. J.; Salomon, R. G. Tetrahedron Lett. 1990, 31, 3813.
22. (e) Suzuki, T.; Sato, O.; Hirama, M. Tetrahedron Lett. 1990, 31, 4747.
23. (f) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Scola, P. M. Tetrahedron Lett. 1992, 33, 1549.
24. (g) Martín, V. S.; Palazón, J. M. Tetrahedron Lett. 1992, 33, 2399.
25. (h) Gung, B. W.; Francis, M. B. J. Org. Chem. 1993, 58, 6177.
26. (i) Mukai, C.; Ikeda, Y.; Sugimoto, Y.; Hanaoka, M. Tetrahedron Lett. 1994, 35, 2179.
27. (j) Mukai, C.; Sugimoto, Y.; Ikeda, Y.; Hanaoka, M. Tetrahedron Lett. 1994, 35, 2183.
28. (k) Palazón, J. M.; Martín, V. S. Tetrahedron Lett. 1995, 36, 3549.
29. (a) Paquette, L. A.; Sweeney, T. J. J. Org. Chem. 1990, 55, 1703.
30. (b) Nicolaou, K. C.; McGarry, D. G.; Somers, P. K.; Kim, B. H.; Ogilvie, W. W.; Yiannikouros, G.; Prasad, C. V. C.; Veale, C. A.; Hark, R. R. J. Am. Chem. Soc. 1990, 112, 6263.
31. (c) Carling, R. W.; Clark, J. S.; Holmes, A. B. J. Chem. Soc., Perkin Trans. 1 1992, 83.
32. (d) Carling, R. W.; Clark, J. S.; Holmes, A. B.; Sartor, D. J. Chem. Soc., Perkin Trans. 1 1992, 95.
33. (e) Fuhry, M. A.; Holmes, A. B.; Marshall, D. R. J. Chem. Soc., Perkin Trans. 1 1993, 2743.
34. (f) Alvarez, E.; Díaz, M. T.; Pérez, R.; Ravelo, J. L.; Regueiro, A.; Vera, J. A.; Zurita, D.; Martín, J. D. J. Org. Chem. 1994, 59, 2848.
35. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Tetrahedron Lett. 1994, 35, 3401.
36. Boger, D. L.; Weinreb, S. N. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, CA, 1987. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, U.K., 1990. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 401-449.
37. Boger, D. L.; Weinreb, S. N. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, CA, 1987. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, U.K., 1990. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 401-449.
38. Boger, D. L.; Weinreb, S. N. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, CA, 1987. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, U.K., 1990. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 401-449.
39. Schmid, C. R.; Bryant, J. D. Org. Synth. 1993, 72, 6.
40. Danishefsky, S. J.; Kobayashi, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 1981. Danishefsky, S. J.; Pearson, W. H.; Harvey, D. F.; Maring, C. J.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1256.
41. Danishefsky, S. J.; Kobayashi, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 1981. Danishefsky, S. J.; Pearson, W. H.; Harvey, D. F.; Maring, C. J.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1256.
42. Krief, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 3, pp 167-168.
43. The aldehydes were prepared according to literature procedures or by simple modification of commercial compounds. See the Supporting Information section.
44. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Tetrahedron 1996, 52, 2167.
45. Bothner-By, A. A.; Stephens, R. L.; Lee, J.; Warren, C. D.; Jeanlo, R. W. J. Am. Chem. Soc. 1984, 106, 81. Bax, A. Davis, D. G., J. Magn. Reson. 1985, 321.
46. Bothner-By, A. A.; Stephens, R. L.; Lee, J.; Warren, C. D.; Jeanlo, R. W. J. Am. Chem. Soc. 1984, 106, 81. Bax, A. Davis, D. G., J. Magn. Reson. 1985, 321.
47. Parker, D. Chem. Rev. 1991, 91, 1441.
48. The LIS studies were conducted comparing the displacement of the signals with that of a racemic mixture, prepared by mixing the enantiomers obtained using aldehyde 5 and its enantiomer in the cycloaddition reaction.
49. Vedejs, E.; Engler, D. A.; Telschow, J. E. J. Org. Chem. 1978, 43, 188.
50. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Synlett 1996, 983.
51. (a) Tsushima, K.; Murai, A. Tetrahedron Lett. 1992, 33, 4345.
52. (b) Robinson, R. A.; Clark, J. S.; Holmes, A. B. J. Am. Chem. Soc. 1993, 115, 10400.
53. (a) Vekemans, J. A. J. M.; Bruyn, R. G. M.; Caris, R. C. H. M.; Kokx, A. J. P. M.; Konings, J. J. H. G.; Godefroi, E. F. J. Org. Chem. 1987, 52, 1093.
54. (b) Hubschwerlen, C.; Specklin, J.-L.; Higelin, J. Org. Synth. 1993, 72, 1.
55. Burton, J. W.; Clark, J. S.; Bendall, J.; Derrer, S.; Stork, T.; Holmes, A. B. J. Am. Chem. Soc. 1996, 118, 6806.
56. We thank Prof. Holmes for informing us of the inconsistencies found in his paper prior to the publication of the retraction.
57. Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958.
58. Burton, J. W.; Clark, J. S.; Derrer, S.; Stork, T. C.; Bendall, J. G.; Holmes, A. B. J. Am. Chem. Soc. 1997, 119, 7483.
59. Krüger, J.; Hoffmann, R. W. J. Am. Chem. Soc. 1997, 119, 7499.