Claisen rearrangement of γ-hydroxyvinyl sulfones via ketene acetal derivatives. A new entry to functionalized (2E,4E)-alkadienoic esters

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5827-5830

  Giovannini, Riccardo ^a   Marcantoni, Enrico ^a   Petrini, Marino ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALKADIENE; ESTER; KETENE DERIVATIVE; SULFONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032490918     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01151-4     Document Type: Article

References (32)

1. 1. For some recent examples see: Tanaka, M.; Nara, F.; Suzuki-Konakai, K.; Hosoya, T.; Ogita, T. J. Am. Chem. Soc. 1997, 119, 7871;
2. b) Millar, J. G.; Tetrahedron Lett. 1997, 38, 7971;
3. c) Gurjar, M.K.; Chakrabarti, A.; Venkateswara Rao, B.; Kumar, P. Tetrahedron Lett. 1997, 38, 6885;
4. d) Kerr, R. G.; Lawry, J. Tetrahedron Lett. 1996, 37, 8306.
5. 2. a) Review: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863;
6. b) Vedejs, E.; Engler, D. A. Tetrahedron Lett. 1977, 1241;
7. c) Huang, Y; Shen, Y.; Zheng, J.; Zhang, S. Synthesis 1985, 57.
8. 3. Cross couplings: a) Abarbri, M.; Parrain, J-L.; Cintrat, J-L.; Duchene, A. Synthesis 1996, 82;
9. b) Lu, X.; Huang, X.; Ma, S. Tetrahedron Lett. 1992, 33, 2535;
10. c) Mitsudo, T.; Zhang, S-W.; Kondo, T.; Watanabe, Y. Tetrahedron Lett. 1992, 33, 341;
11. Isomerizations: d) Ma, D.; Lu, X. Tetrahedron 1990, 46, 3189 and 6919;
12. Carbonylations: e) Imada, H.; Alper, H. J. Org. Chem. 1996, 61, 6766;
13. f) Huh, K.; Orita, A.; Alper, H. J. Org. Chem. 1993, 58, 6956;
14. Condensations: g) Herscovici, J.; Boumaiza, L.; Antonakis, K. Tetrahedron Lett. 1991, 32, 1791;
15. Homologations: h) Bernabeu, M. C.; Chinchilla, R.; Najera, C. Tetrahedron Lett. 1995, 36, 3901;
16. i) Lewis, N.; McKen, P. W.; Taylor, R. K. J. Synlett 1991, 898.
17. 4. Trost, B. M.; Lautens, M.; Peterson, B. Tetrahedron Lett. 1983, 24, 4525.
18. 5. Mandai, T.; Moriyama, T.; Tsujimoto, K.; Kawada, M.; Otera, J. Tetrahedron Lett. 1986, 27, 603.
19. 6. Plobeck, N.; Backvall, J. E. J. Org. Chem. 1991, 56, 4508.
20. 7. a) Dominguez, E.; Carretero, J. C. Tetrahedron 1990, 46, 7197;
21. b) Trost, B. M.; Grese, T. A. J. Org. Chem. 1991, 46, 3189;
22. for a recent synthetic application of γ-oxygenated vinyl sulfones see: c) Alonso, I.; Carretero, J. C.; Garrido, J. L.; Magro, V.; Pedregal, C. J. Org. Chem. 1997, 62, 5682.
23. 8. Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T-T.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741.
24. 9. Reviews: a) Wipf, P. Claisen Rearrangement in Comprehensive Organic Synthesis Trost, B. M.; Fleming, I.; Paquette, L. A. Eds. Pergamon Oxford, 1991, Vol. 5, p. 827;
25. b) Ziegler, F. E. Chem Rev. 1988, 88, 1423;
26. c) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 22, 1.
27. 10. The observed preference for the E stereoisomer is probably a consequence of a chair-like transition state in which the substituents occupy a pseudo-equatorial orientation. (formula presented)
28. 11. a) Burrows, C. J.; Carpenter, B. K. J. Am. Chem. Soc. 1981, 103, 6984;
29. b) Aviyente, V.; Yoo, H. N.; Houk, K. N. J. Org. Chem. 1997, 62, 6121.
30. 12. Welch, J. T.; Eswarakrishnan, S.J. Org. Chem. 1985, 50, 5909.
31. 13. A coupling constant J= 15.3 Hz has been observed for the C-2 proton.
32. +), 230, 201, 139, 111, 67.