The Baylis-Hillman reaction: One-pot facile synthesis of 2,4-functionalized 1,4-pentadienes

Journal of Organic Chemistry

Volumn 67, Issue 20, 2002, Pages 7135-7137

  Basavaiah, Deevi ^a   Sharada, Duddu S ^a   Kumaragurubaran, Nagaswamy ^a   Reddy, Ravi Mallikarjuna ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BAYLIS-HILLMAN REACTION;

OLEFINS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

1,4 PENTADIENE; 2 (BROMOMETHYL)PROP 2 ENOATE DERIVATIVE; ALKENE DERIVATIVE; ALKYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0037019994     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0257952     Document Type: Article

References (42)

1. a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
2. (b) Basavaiah, D.; Dharmarao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001.
3. (c) Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; vol. 51, pp 201-350.
4. (d) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049.
5. a) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317.
6. (b) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219.
7. (c) Aggarwal, V. K.; Mereu, A. Chem. Commun. 1999, 2311.
8. (d) Räcker, R.; Döring, K.; Reiser, O. J. Org. Chem. 2000, 65, 6932.
9. (e) Ayed, T. B.; Villiéras, J.; Amri, H. Tetrahedron 2000, 56, 805.
10. (f) Trost, B. M.; Tsui, H.-C.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 3534.
11. (g) Kim, J. N.; Lee, K. Y.; Kim, H. S.; Kim, T. Y. Org. Lett. 2000, 2, 343.
12. (h) Katoaka, T.; Kinoshita, H.; Kinoshita, S.; Iwamura, T.; Watanabe, S.-I. Angew. Chem., Int. Ed. 2000, 39, 2358.
13. (i) Li, G.; Wei, H.-X.; Gao, J. J.; Caputo, T. D. Tetrahedron Lett. 2000, 41, 1.
14. (j) Yu, C.; Liu, B.; Hu, L. J. Org. Chem. 2001, 66, 5413.
15. (k) Kim, J. N.; Kim, H. S.; Gong, J. H.; Chung, Y. M. Tetrahedron Lett. 2001, 42, 8341.
16. (l) Lee, W.-D.; Yang, K.-S.; Chen, K. Chem. Commun. 2001, 1612.
17. (m) Aggarwal, V. K.; Castro, A. M. M.; Mereu, A.; Adams, H. Tetrahedron Lett. 2002, 43, 1577.
18. (n) Shi, M.; Jiang, J.-K.; Li, C.-Q. Tetrahedron Lett. 2002, 43, 127.
19. (o) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
20. a) Basavaiah, D.; Gowriswari, V. V. L. Tetrahedron Lett. 1986, 27, 2031.
21. (b) Basavaiah, D.; Krishnamacharyulu, M.; Suguna Hyma, R.; Sarma, P. K. S.; Kumaragurubaran, N. J. Org. Chem. 1999, 64, 1197.
22. (c) Basavaiah, D.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron Lett. 2001, 42, 85.
23. (d) Basavaiah, D.; Kumaragurubaran, N.; Tetrahedron Lett. 2001, 42, 477.
24. (e) Basavaiah, D.; Satyanarayana, T. Org. Lett. 2001, 3, 3619.
25. a) Nicolaou, K. C.; Ramphal, J. Y.; Petasis, N. A.; Serhan, C. N. Angew. Chem., Int. Ed. Engl. 1991, 30, 1100.
26. (b) Andrey, O.; Glanzmann, C.; Landais, Y.; Parra-Rapado, L. Tetrahedron 1997, 53, 2835.
27. (c) Durand, S.; Parrain, J.-L.; Santelli, M. J. Chem. Soc., Perkin Trans. 1 2000, 253.
28. a) Eilbracht, P.; Acker, M.; Totzauer, W. Chem. Ber. 1983, 116, 238.
29. (b) Grigg, R.; Dorrity, M. J.; Heaney, F.; Malone, J. F.; Rajviroongit, S.; Sridharan, V.; Surendrakumar, S. Tetrahedron 1991, 47, 8297.
30. (c) Roulet, J.-M.; Deguin, B.; Vogel, P. J. Am. Chem. Soc. 1994, 116, 3639.
31. (d) Denmark, S. E.; Guagnano, V.; Dixon, J. A.; Stolle, A. J. Org. Chem. 1997, 62, 4610.
32. (e) Prasad, A. S. B.; Knochel, P. Tetrahedron 1997, 53, 16711.
33. (a) Matsushita, H.; Negishi, E. J. Am. Chem. Soc. 1981, 103, 2882.
34. (b) Ohm, S.; Bauml, E.; Mayr, H. Chem. Ber. 1991, 124, 2785.
35. (c) Agrios, K. A.; Srebnik, M. J. Org. Chem. 1994, 59, 5468.
36. (d) Kobayashi, Y.; Ikeda, E. J. Chem. Soc., Chem. Commun. 1994, 1789.
37. (e) Matsuhashi, H.; Hatanaka, Y.; Kuroboshi, M.; Hiyama, T. Tetrahedron Lett. 1995, 36, 1539.
38. (f) Takai, K.; Yamada, M.; Odaka, H.; Utimoto, K.; Fujii, T.; Furukawa, I. Chem. Lett. 1995, 315.
39. (g) Harra R.; Nishihara, Y.; Landre, P. D.; Takahashi, T. Tetrahedron Lett. 1997, 38, 447
40. (h) Klaps, E.; Schmid, W. J. Org. Chem. 1999, 64, 7537.
41. 3c
42. Villieras, J.; Rambaud, M. Synthesis 1982, 924.