Nucleophilic catalysis via phosphine conjugate addition: Vinyl sulfones as reacting partners in catalytic cross-Michael cycloisomerization

Synthesis

Volumn , Issue 15, 2004, Pages 2579-2585

  Luis, Ana Liza ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Conjugate addition; Cycloisomerization; Nucleophilic catalysis; Phosphine; Vinyl sulfone

Indexed keywords

ADDITION REACTIONS; CATALYSIS; ISOMERIZATION; MOLECULAR STRUCTURE;

PHOSPHINE CONJUGATE ADDITION; SINGLE CONSTITUTIONAL ISOMERS;

PHOSPHORUS COMPOUNDS;

PHOSPHINE DERIVATIVE; SULFONE; TRIBUTYLPHOSPHINE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLSULFONE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CONJUGATE; CROSS MICHAEL CYCLOISOMERIZATION; CYCLOISOMERIZATION; ISOMER; ISOMERIZATION; MICHAEL ADDITION; NUCLEOPHILIC CATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 7644234128     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831191     Document Type: Article

References (59)

1. (a) Baik, T.-G.; Luiz, A.-L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112.
2. (b) Wang, L.-C.; Jang, H.-Y.; Roh, Y.; Schultz, A. J.; Wang, X.; Lynch, V.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448.
3. (c) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
4. (d) Huddleston, R. R.; Krische, M. J. Org. Lett. 2003, 5, 1143.
5. (e) Huddleston, R. R.; Cauble, D. F.; Krische, M. J. J. Org. Chem. 2003, 68, 11.
6. (f) Marriner, G. A.; Garner, S. A.; Jang, H.-Y.; Krische, M. J. J. Org. Chem. 2004. 69, 1380.
7. (g) Koech, P. K.; Krische, M. J. Org. Lett. 2004, 6, 691.
8. (a) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
9. (b) Bocknack, B. M.; Wang, L.-C.; Krische, M. J. Proc. Nat. Acad. Sci. U.S.A. 2004, 101, 5421.
10. (c) Agapiou, K.; Cauble, D. F.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4528.
11. (a) Wang, L.-C.; Luiz, A.-L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
12. (b) Agapiou, K.; Krische, M. J. Org. Lett. 2003, 5, 1737.
13. (c) Jellerichs, B. G.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 7758.
14. (d) Koech, P. K.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 5350.
15. For an authoritative review, see: Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
16. Stewart, I. C.; Bergman, R. G.; Toste, F. D. J. Am. Chem. Soc. 2003, 125, 8696.
17. (a) Trost, B. M.; Kazmaier, U. J. Am. Chem. Soc. 1992, 114, 7933.
18. (b) Guo, C.; Lu, X. J. Chem. Soc., Perkin Trans. 1 1993, 1921.
19. (a) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 62, 5670.
20. (b) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595.
21. (a) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906.
22. (b) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461.
23. (c) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836.
24. (d) Xu, Z.; Lu, X. Tetrahedron Lett. 1999, 40, 549.
25. (e) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031.
26. (f) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901.
27. (a) Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682.
28. (b) Wang, J.-C.; Krische, M. J. Angew. Chem. Int. Ed. 2003, 42, 5855.
29. Zhu, X.-F.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716.
30. Jellerichs, B. G.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 7758.
31. Evans, C. A.; Miller, S. J. J. Am. Chem. Soc. 2003, 125, 12394.
32. (a) Gong, J. H.; Kim, H. R.; Ryu, E. K.; Kirn, J. N. Bull. Kor. Chem. Soc. 2002, 23, 789.
33. (b) Kim, J. N.; Lee, H. J.; Lee, K. Y.; Gong, J. H. Synlett 2002, 173.
34. (c) Basavaiah, D.; Kumaragurubaran, N.; Sharada, D. S.; Reddy, R. M. Tetrahedron 2001, 57, 8167.
35. (d) Ciclosi, M.; Fava, C.; Galeazzi, R.; Orena, M.; Sepulveda-Arques, J. Tetrahedron Lett. 2002, 43, 2199.
36. (e) Kim, J. N.; Lee, H. J.; Gong, J. H. Tetrahedron Lett. 2002, 43, 9141.
37. Gong, J. H.; Im, Y. J.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2002, 43, 1247.
38. Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
39. Brown, P. M.; Kappel, N.; Murphy, P. J. Tetrahedron Lett. 2002, 43, 8707.
40. For selected examples of the Rauhut-Currier reaction, see: (a) Rauhut, M. M.; Currier, H. US Patent 3074999, 1963.
41. (b) McClure, J. D. J. Org. Chem. 1970, 35, 3045.
42. (c) Basavaiah, D.; Gowriswari, V. V. L.; Bharathi, T. K. Tetrahedron Lett. 1987, 28, 4591.
43. (d) Drewes, S. E.; Emslie, N. D.; Karodia, N. Synth. Commun. 1990, 20, 1915.
44. (e) Jenner, G. Tetrahedron Lett. 2000, 41, 3091.
45. (a) Mergott, D. J.; Frank, S. A.; Roush, W. R. Org. Lett. 2002. 4, 3157.
46. (b) Agapiou, K.; Krische, M. J. Org. Lett. 2003. 5, 1737.
47. (c) Mergot, J. L.; Roush, W. R. Org. Lett. 2003, 5, 4223.
48. For a review, see: (a) Najera, C.; Yus, M. Tetrahedron 1999, 55, 10547.
49. (b) Prilezhaeva, E. N. Russ. Chem. Rev. 2001, 70, 897.
50. (c) Carretero, J. C.; Arrayas, R. G.; Buezo, N. D.; Garrido, J. L.; Alonso, I.; Adrio, J. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 153, 259.
51. (d) Magnus, P. D. Tetrahedron 1977, 33, 2019.
52. (a) Ager, D. J. J. Chem. Soc., Perkin Trans. 1 1986, 183.
53. (b) Van Leusen, A. M.; Reith, B. A.; Iedema, A. J. W.; Strating, J. Red. Trav. Chim. Pays-Bas 1972, 91, 37.
54. (c) Simpkins, N. S. Tetrahedron 1990, 46, 6951.
55. Jang, W. B.; Jeon, H. J.; Oh, D. Y. Synth. Commun. 1998, 28, 1253.
56. Keck, G. E.; Boden, E. P.; Mabury, S. A. J. Org. Chem. 1985, 50, 709.
57. Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
58. Keck, G. E.; Welch, D. S. Org. Lett. 2002, 4, 3687.
59. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.