Organomediated Morita-Baylis-Hillman cyclization reactions

Journal of the American Chemical Society

Volumn 127, Issue 29, 2005, Pages 10168-10169

  Krafft, Marie E ^a   Haxell, Thomas F N ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; MESYLIC ACID; TOLUENESULFONIC ACID DERIVATIVE;

ALLYLATION; ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; MORITA REACTION; PHASE TRANSITION; REACTION ANALYSIS;

EID: 22944474675     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052146+     Document Type: Article

References (27)

1. Baylis, A. B.; Hillman, M. E. D.; German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174q.
2. (a) Morita, K. Japan Patent 6803364, 1968; Chem. Abstr. 1968, 69, 58828s.
3. (b) Morita, K.; Suzuki, Z.; Hirose, H. Bull Chem. Soc. Jpn. 1968, 41, 2815.
4. For reviews, see: (a) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
5. (b) Ciganek, E. Org. React. 1997, 51, 201.
6. (c) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
7. (d) Langer, P. Angew. Chem., Int. Ed 2000, 39, 3049.
8. (a) Drewes, S. E.; Njamela, O. L.; Emslie, N. D.; Ramesar, N.; Field, J. S. Synth. Commun. 1993, 23, 2807.
9. (b) Roth, F.; Gygax, P.; Fráter, G. Tetrahedron Lett. 1992, 33, 1045.
10. (c) Black, G. P.; Dinon, F.; Fratucello, S.; Murphy, P. J.; Nielson, M.; Williams, H. L.; Walshe, N. D. A. Tetrahedron Lett. 1997, 38, 8561.
11. (d) Dinon, F.; Richards, E.; Murphy, P. J.; Hibbs, D. E.; Hursthouse, M. B.; Mailik, K. M. A. Tetrahedron Lett. 1999, 40, 3279.
12. (e) Richards, E. L.; Murphy, P. J.; Dinon, F.; Fratucello, S.; Brown, P. M.; Gelbrich, T.; Hursthouse, M. B. Tetrahedron 2001, 57, 7771.
13. (f) Jung, E. Y.; Yang, X.; Kim, H. J.; Koo, S. Chem. Commun. 2004, 236.
14. (a) Wang, L.-C.; Luis, A.-L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
15. (b) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
16. (a) Basavaiah, D.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron Lett. 2001, 42, 85.
17. (b) Basavaiah, D.; Sharada, D. S.; Kumaragurubaran, N.; Reddy, R. M. J. Org. Chem. 2002, 67, 7135.
18. Jellerichs, B. G.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 7758.
19. Lee, H. Y.; Kim, Y. J. Am. Chem. Soc. 2003, 125, 10156.
20. (a) Rauhut, M. M.; Currier, H. U.S. Patent 3074999, 1963; Chem. Abstr. 1963, 58, 11224a.
21. (b) Yamada, Y. M. A.; Ikegami, S. Tetrahedron Lett. 2000, 41, 2165.
22. (c) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
23. (d) Cho, C.-W.; Krische, M. J. Angew. Chem., Int. Ed. 2004, 43, 6689.
24. (e) Koech, P. K.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 5350.
25. (f) Cho, C. W.; Kong, J.-R. Krische, M. J. Org. Lett. 2004, 6, 1337.
26. Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
27. 3NCl (10 mol %) and stirred until complete (2 h).