Highly stereoselective vinylogous pummerer reaction mediated by Me 3SiX

Organic Letters

Volumn 7, Issue 1, 2005, Pages 19-22

  García Ruano, Jose L ^a   Alemán, José ^a   Aranda, M Teresa ^a   Arévalo, María J ^b   Padwa, Albert ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ALCOHOL DERIVATIVE; BENZYL DERIVATIVE; HALIDE; OXYGEN DERIVATIVE; SILICON DERIVATIVE; SULFUR DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; ENANTIOSELECTIVITY; PUMMERER REACTION; STEREOCHEMISTRY;

EID: 12344267165     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048054r     Document Type: Article

References (36)

1. Pummerer, R. Chem. Ber. 1909, 42, 2282.
2. (a) De Lucchi, O.; Miotti, U.; Modena, G. In Organic Reactions; Paquette, L. A., Ed.; Wiley: 1991; Chapter 3, p 157.
3. (b) Grierson, D. S.; Husson, H. P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 6, p 909.
4. (c) Kennedy, M.; McKervey, M. A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 7, p 193.
5. (a) Padwa, A.; Gunn, D. E.; Osterhout, H. M. Synthesis 1997, 1353.
6. (b) Padwa, A. Pure Appl. Chem. 2003, 75, 47.
7. (a) Russell, G. A.; Mikol, G. J. In Mechanisms of Molecular Migration; Thyagaragan, B. S., Ed.; Wiley: New York, 1968; Vol. 1, p 157.
8. (b) Oae, S.; Numata, T. The Pummerer Type of Reactions. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. E., Eds.; Elsevier: New York, 1980; Vol. 5, Chapter 2.
9. (c) Marino, J. P. In Topics in Sulfur Chemistry; Senning, A., Ed.; George Thieme: Stuttgart, Germany, 1976; Vol. 1, p 1.
10. (a) Padwa, A. Phosphorous, Sulfur, Silicon 1999, 153, 23.
11. (b) Padwa, A.; Danca, D. M.; Ginn, J. D.; Lynch, S. M. J. Braz. Chem. Soc. 2001, 12, 571.
12. (c) Padwa, A.; Bur, S. K.; Danca, D. M.; Ginn, J. D.; Lynch, S. M. Synlett 2002, 851.
13. Bur, S. K.; Padwa, A. Chem. Rev. 2004, 104, 2401.
14. Leading references to vinylogous Pummerer reactions can be found in: (a) Padwa, A.; Kuethe, J. T. J. Org. Chem. 1998, 63, 4256. (b) Marino, J. P.; Bogdan, S.; Kimura, K. J. Am. Chem. Soc. 1992, 114, 5566.
15. Leading references to vinylogous Pummerer reactions can be found in: (a) Padwa, A.; Kuethe, J. T. J. Org. Chem. 1998, 63, 4256. (b) Marino, J. P.; Bogdan, S.; Kimura, K. J. Am. Chem. Soc. 1992, 114, 5566.
16. For a new variant of the vinylogous Pummerer reaction, see: (a) Feldman, K. S.; Vidulova, D. B. Org. Lett. 2004, 6, 1869. (b) Feldman, K. S.; Karatjas, A. G. Org. Lett. 2004, 6, 2849.
17. For a new variant of the vinylogous Pummerer reaction, see: (a) Feldman, K. S.; Vidulova, D. B. Org. Lett. 2004, 6, 1869. (b) Feldman, K. S.; Karatjas, A. G. Org. Lett. 2004, 6, 2849.
18. García Ruano, J. L.; Alemán, J.; Padwa, A. Org. Lett. 2004, 6, 1757.
19. For some examples of the tin-Pummerer reaction, see: (a) Beddoes, R. L.; MacLeod, D.; Moorcroft, D.; Quayle, P.; Zhao, Y.; Davies, G. M. Tetrahedron Lett. 1992, 33, 417. (b) Pohmakotr, M.; Sithikanchanakul, S. Tetrahedron Lett. 1989, 30, 6773.
20. For some examples of the tin-Pummerer reaction, see: (a) Beddoes, R. L.; MacLeod, D.; Moorcroft, D.; Quayle, P.; Zhao, Y.; Davies, G. M. Tetrahedron Lett. 1992, 33, 417. (b) Pohmakotr, M.; Sithikanchanakul, S. Tetrahedron Lett. 1989, 30, 6773.
21. For some leading references, see: (a) Ponzo, V. L.; Kaufman, T. S. Synlett 2002, 1128. (b) Hillier, M. C.; Desrosiers, J. N.; Marcoux, J. F.; Grabowski, E. J. J. Org. Lett. 2004, 6, 573. (c) Nakamura, S.; Oda, M.; Yasuda, H.; Toru, T. Tetrahedron 2001, 57, 8459.
22. For some leading references, see: (a) Ponzo, V. L.; Kaufman, T. S. Synlett 2002, 1128. (b) Hillier, M. C.; Desrosiers, J. N.; Marcoux, J. F.; Grabowski, E. J. J. Org. Lett. 2004, 6, 573. (c) Nakamura, S.; Oda, M.; Yasuda, H.; Toru, T. Tetrahedron 2001, 57, 8459.
23. For some leading references, see: (a) Ponzo, V. L.; Kaufman, T. S. Synlett 2002, 1128. (b) Hillier, M. C.; Desrosiers, J. N.; Marcoux, J. F.; Grabowski, E. J. J. Org. Lett. 2004, 6, 573. (c) Nakamura, S.; Oda, M.; Yasuda, H.; Toru, T. Tetrahedron 2001, 57, 8459.
24. For reaction with carbonyl groups, see: (a) García Ruano, J. L.; Aranda, M.; Carreño, M. C.; Toledo, M. A. Angew. Chem., Int. Ed. 2000, 39, 2736. For reaction with imines, see: (b) García Ruano, J. L.; Alemán, J.; Soriano, J. F. Org. Lett. 2003, 5, 677. (c) García Ruano, J. L.; Alemán, J. Org. Lett. 2003, 5, 4513.
25. For reaction with carbonyl groups, see: (a) García Ruano, J. L.; Aranda, M.; Carreño, M. C.; Toledo, M. A. Angew. Chem., Int. Ed. 2000, 39, 2736. For reaction with imines, see: (b) García Ruano, J. L.; Alemán, J.; Soriano, J. F. Org. Lett. 2003, 5, 677. (c) García Ruano, J. L.; Alemán, J. Org. Lett. 2003, 5, 4513.
26. For reaction with carbonyl groups, see: (a) García Ruano, J. L.; Aranda, M.; Carreño, M. C.; Toledo, M. A. Angew. Chem., Int. Ed. 2000, 39, 2736. For reaction with imines, see: (b) García Ruano, J. L.; Alemán, J.; Soriano, J. F. Org. Lett. 2003, 5, 677. (c) García Ruano, J. L.; Alemán, J. Org. Lett. 2003, 5, 4513.
27. García Ruano, J. L.; Alemán, J.; Aranda, M. T.; Fernández-Ibáñez, M. A.; Rodríguez-Fernández, M. M.; Maestro, M. C. Tetrahedron 2004, 60, 10067.
28. 3SiX have also been used in some cases to produce the normal Pummerer reaction; see: Tokitoh, N.; Igarashi, Y.; Ando, W. Tetrahedron Lett. 1987, 28, 5903.
29. Under similar conditions, ethylphenylsulfoxide underwent C-silylation; see: Miller, R. D.; Hassig, R. Tetrahedron Lett. 1984, 25, 5351. An alternative vinylogous silicon-Pummerer rearrangement could have also been invoked (see: Brook, A. G.; Anderson, D. G. Can. J. Chem. 1968, 46, 2115. Shainyan, B. A.; Kipichenko, S. V.; Freeman, F. J. Am. Chem. Soc. 2004, 124, 11456) to explain the stereochemical results encountered. However, we could not obtain any evidence indicating the formation of a C-silyl derivative, even when working in the presence of HMPA, which would enhance the nucleophilicity at the carbon atom.
30. Under similar conditions, ethylphenylsulfoxide underwent C-silylation; see: Miller, R. D.; Hassig, R. Tetrahedron Lett. 1984, 25, 5351. An alternative vinylogous silicon-Pummerer rearrangement could have also been invoked (see: Brook, A. G.; Anderson, D. G. Can. J. Chem. 1968, 46, 2115. Shainyan, B. A.; Kipichenko, S. V.; Freeman, F. J. Am. Chem. Soc. 2004, 124, 11456) to explain the stereochemical results encountered. However, we could not obtain any evidence indicating the formation of a C-silyl derivative, even when working in the presence of HMPA, which would enhance the nucleophilicity at the carbon atom.
31. Under similar conditions, ethylphenylsulfoxide underwent C-silylation; see: Miller, R. D.; Hassig, R. Tetrahedron Lett. 1984, 25, 5351. An alternative vinylogous silicon-Pummerer rearrangement could have also been invoked (see: Brook, A. G.; Anderson, D. G. Can. J. Chem. 1968, 46, 2115. Shainyan, B. A.; Kipichenko, S. V.; Freeman, F. J. Am. Chem. Soc. 2004, 124, 11456) to explain the stereochemical results encountered. However, we could not obtain any evidence indicating the formation of a C-silyl derivative, even when working in the presence of HMPA, which would enhance the nucleophilicity at the carbon atom.
32. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
33. This behavior is also found with the alkylation of other sulfinyl carbanions; see: Drabowicz, J.; Kielbasinski, P.; Mikolajczky, M. In The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C., Eds.; Wiley: Chichester, 1988; pp 305-317.
34. There are some examples in the literature where substitution rather than elimination was observed with phenylethyl-substituted systems; see: Solladié-Cavallo, A.; Martin-Cabrejas, L. M.; Caravatti, G.; Lang, M. Tetrahedron: Asymmetry 2001, 12, 967.
35. Stabilization of the carbanionic intermediate by the nitrogen atom may be responsible for the lack of reactivity of 19.
36. 2) or at 120°C (toluene) in a sealed reaction vessel, thereby indicating that it does not undergo a thermal silicon-Pummerer rearrangement.