Acyclic Stereoselection in the Ortho Ester Claisen Rearrangement

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 1976-1985

  Daub, G William ^a   Edwards, James P ^a   Okada, Carol R ^a   Allen, Jana Westran ^a   Maxey, Claudia Tata ^a   Wells, Matthew S ^a   Goldstein, Alexandra S ^a   Dibley, Michael J ^a   Wang, Clarence J ^a   Ostercamp, Daniel P ^a   Chung, Steven ^a   Cunningham, Paula Shanklin ^a   Berliner, Martin A ^a  

^a HARVEY MUDD COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000649099     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9614250     Document Type: Article

References (45)

1. Review articles on the Claisen rearrangement include: (a) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (b) Ziegler, F. E. Acc. Chem. Res. 1977, 10, 227. (c) Bennett, G. B. Synthesis 1977, 589.
2. Review articles on the Claisen rearrangement include: (a) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (b) Ziegler, F. E. Acc. Chem. Res. 1977, 10, 227. (c) Bennett, G. B. Synthesis 1977, 589.
3. Review articles on the Claisen rearrangement include: (a) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (b) Ziegler, F. E. Acc. Chem. Res. 1977, 10, 227. (c) Bennett, G. B. Synthesis 1977, 589.
4. For a preliminary report on aspects of this study see: Daub, G. W.; Shanklin, P. L.; Tata, C. J. Org. Chem. 1986, 51, 3402.
5. Hansen, H. J.; Schmid, H. Tetrahedron 1974, 30, 1959.
6. Doering, W. v. E.; Roth, W. R. Tetrahedron 1962, 18, 67.
7. All structures, while drawn as a single enantiomer, represent racemates. The syn / anti stereostructural notation proposed by Masamune is used in this paper: Masamune, S.; Ali, S. A.; Snitman, D. L.; Garvey, D. S. Angew. Chem., Int. Ed. Engl. 1980, 19, 557.
8. (a) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
9. (b) Ireland, R. E., Thaisrivongs, S.; Wilcox, C. S. J. Am. Chem. Soc. 1980, 102, 1155.
10. Sucrow, W.; Richter, W. Chem. Ber. 1971, 104, 3679.
11. Bartlett, P. A.; Hahne, W. F. J. Org. Chem. 1979, 44, 882.
12. Ficini, J.; Barbara, C. Tetrahedron Lett. 1971, 104, 3679.
13. Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741.
14. (a) Daub, G. W.; Sanchez, M. G.; Cromer, R. A.; Gibson, L. G. J. Org. Chem. 1982, 47, 743.
15. (b) Daub, G. W.; McCoy, M. A.; Sanchez, M. G.; Carter, J. S. J. Org. Chem. 1983, 48, 3876.
16. (a) Stork, G.; Raucher, S. J. Am. Chem. Soc. 1976, 98, 1583.
17. (b) Bolton, I. J.; Harrison, R. G.; Lythgoe, B. J. Chem. Soc., C 1971, 2950.
18. (c) Raucher, S.; Hwang, K. J.; McDonald, J. E. Tetrahedron Lett. 1979, 3057.
19. (d) Raucher, S.; McDonald, J. E.; Lawrence, R. F. Tetrahedron Lett. 1980, 4335.
20. (e) Daub, G. W.; Teramura, D. H.; Bryant, K. E.; Burch, M. T. J. Org. Chem. 1981, 46, 1485.
21. (f) Daub, G. W.; Lunt, S. R. Tetrahedron Lett. 1983, 4397.
22. Faulkner, D. J.; Peterson, M. R. Tetrahedron Lett. 1969, 3243.
23. The presence of such a 1,3-diaxial interaction in the transition state does not preclude such a pathway from competing, but it does demand that other pathways be sterically more demanding. In the Present case, the competing pathway is sterically less demanding and predominates. See Ziegler, F. E.; Klein, S. I.; Pati, U. K.; Wang, T.-F. J. Am. Chem. Soc. 1985, 107, 2730.
24. A similar interaction has been described by Parker, K. A.; Farmar, J. G. Tetrahedron Lett. 1985, 3655.
25. For examples where selectivity relative to a more distal center is induced by such an interaction, see: (a) White, J. D.; Amedio, J. C. J. Org. Chem. 1989, 54, 736. (b) Wovkulich, P. M.; Tang, P. C.; Chadha, N. K.; Batcho, A. D.; Barrish, J. C.; Uskokovic, M. R. J. Am. Chem. Soc. 1989, 111, 2596.
26. For examples where selectivity relative to a more distal center is induced by such an interaction, see: (a) White, J. D.; Amedio, J. C. J. Org. Chem. 1989, 54, 736. (b) Wovkulich, P. M.; Tang, P. C.; Chadha, N. K.; Batcho, A. D.; Barrish, J. C.; Uskokovic, M. R. J. Am. Chem. Soc. 1989, 111, 2596.
27. Mori, K; Matsui, M. Tetrahedron 1970, 26, 2801.
28. Sreekumar, C.; Darst, K. P.; Still, W. C. J. Org. Chem. 1980, 45, 4260.
29. Katzenellenbogen, J. A.; Christy, K. J. J. Org. Chem. 1974, 39, 3315.
30. The detection limits for capillary GC analysis were <±1%.
31. Daub, G. W., Griffith, D. A. Tetrahedron Lett. 1986, 6311.
32. (a) Arsenault, G. P.; Althaus, J. R.; Divekar, P. V. J. Chem. Soc., D 1969, 1414.
33. (b) Moreau, S.; Lablanche-Combier, A.; Biguet, J.; Foulon, C.; Delfosse, M. J. Org. Chem. 1982, 47, 2358.
34. For other syntheses of botryodiplodin see: (a) McCurry, P. M., Jr.; Abe, K. J. Am. Chem. Soc. 1973, 95, 5824. (b) McCurry, P. M., Jr.; Abe, K. Tetrahedron Lett. 1973, 4103. (c) Mukaiyama, T.; Wada, M.; Hanna, J.; Chem. Lett. 1974, 94, 1181. (d) Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309. (e) Kurth, M. J.; Yu, C.-M. J. Org. Chem. 1985, 50, 1840. (f) Rehnberg, N.; Frejd, T.; Magnusson, G. Tetrahedron Lett. 1987, 3589.
35. For other syntheses of botryodiplodin see: (a) McCurry, P. M., Jr.; Abe, K. J. Am. Chem. Soc. 1973, 95, 5824. (b) McCurry, P. M., Jr.; Abe, K. Tetrahedron Lett. 1973, 4103. (c) Mukaiyama, T.; Wada, M.; Hanna, J.; Chem. Lett. 1974, 94, 1181. (d) Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309. (e) Kurth, M. J.; Yu, C.-M. J. Org. Chem. 1985, 50, 1840. (f) Rehnberg, N.; Frejd, T.; Magnusson, G. Tetrahedron Lett. 1987, 3589.
36. For other syntheses of botryodiplodin see: (a) McCurry, P. M., Jr.; Abe, K. J. Am. Chem. Soc. 1973, 95, 5824. (b) McCurry, P. M., Jr.; Abe, K. Tetrahedron Lett. 1973, 4103. (c) Mukaiyama, T.; Wada, M.; Hanna, J.; Chem. Lett. 1974, 94, 1181. (d) Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309. (e) Kurth, M. J.; Yu, C.-M. J. Org. Chem. 1985, 50, 1840. (f) Rehnberg, N.; Frejd, T.; Magnusson, G. Tetrahedron Lett. 1987, 3589.
37. For other syntheses of botryodiplodin see: (a) McCurry, P. M., Jr.; Abe, K. J. Am. Chem. Soc. 1973, 95, 5824. (b) McCurry, P. M., Jr.; Abe, K. Tetrahedron Lett. 1973, 4103. (c) Mukaiyama, T.; Wada, M.; Hanna, J.; Chem. Lett. 1974, 94, 1181. (d) Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309. (e) Kurth, M. J.; Yu, C.-M. J. Org. Chem. 1985, 50, 1840. (f) Rehnberg, N.; Frejd, T.; Magnusson, G. Tetrahedron Lett. 1987, 3589.
38. For other syntheses of botryodiplodin see: (a) McCurry, P. M., Jr.; Abe, K. J. Am. Chem. Soc. 1973, 95, 5824. (b) McCurry, P. M., Jr.; Abe, K. Tetrahedron Lett. 1973, 4103. (c) Mukaiyama, T.; Wada, M.; Hanna, J.; Chem. Lett. 1974, 94, 1181. (d) Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309. (e) Kurth, M. J.; Yu, C.-M. J. Org. Chem. 1985, 50, 1840. (f) Rehnberg, N.; Frejd, T.; Magnusson, G. Tetrahedron Lett. 1987, 3589.
39. For other syntheses of botryodiplodin see: (a) McCurry, P. M., Jr.; Abe, K. J. Am. Chem. Soc. 1973, 95, 5824. (b) McCurry, P. M., Jr.; Abe, K. Tetrahedron Lett. 1973, 4103. (c) Mukaiyama, T.; Wada, M.; Hanna, J.; Chem. Lett. 1974, 94, 1181. (d) Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309. (e) Kurth, M. J.; Yu, C.-M. J. Org. Chem. 1985, 50, 1840. (f) Rehnberg, N.; Frejd, T.; Magnusson, G. Tetrahedron Lett. 1987, 3589.
40. Prepared from cis-2-butene-1,4-diol according to Czernecki, S.; Georgoulis, C.; Proveloenghiou, C. Tetrahedron Lett. 1976, 3535.
41. The authors would like to thank the Chemistry Departments of the University of California, Irvine, and Pomona College for the use of their ozone generators.
42. 1H NMR at 200 MHz.
43. Reist, E. J.; Bartuska, V. J.; Goodman, L.; Johnson, E. J. Org. Chem. 1964, 29, 3725.
44. Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K.; Huber, W. J. Am. Chem. Soc. 1969, 91, 5675.
45. 1H NMR revealed these to be the α-anomer of botryodiplodin acetate (2α-47), the β-anomer of botryodiplodin acetate (2β-47), the β-anomer of epibotryodiplodin acetate (2β-48), and the α-anomer of epibotryodiplodin acetate (2α-48), respectively.