A practical preparation of 2-hydroxymethyl-2-cyclopenten-1-one by Morita-Baylis-Hillman reaction

Synthesis

Volumn , Issue 18, 2005, Pages 3035-3038

  Ito, Hisanaka ^a   Takenaka, Yosuke ^a   Fukunishi, Shouhei ^a   Iguchi, Kazuo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Addition reactions; Carbocycles; Catalysis; Enones; Phosphorus

Indexed keywords

ADDITION REACTIONS; CATALYSIS; FORMALDEHYDE; PHOSPHORUS; SOLVENTS; SYNTHESIS (CHEMICAL);

CARBOCYCLES; ENONES;

KETONES;

2 HYDROXYMETHYL 2 CYCLOPENTEN 1 ONE; CYCLOPENTENE DERIVATIVE; DIMETHYLPHENYLPHOSPHINE; PHOSPHINE DERIVATIVE; TRIBUTYLPHOSPHINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MORITA BAYLIS HILLMAN REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 28344456399     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-916030     Document Type: Article

References (38)

1. (a) Joseph, E.; Eiseman, J. L.; Hamilton, D. S.; Wang, H.; Tak, H.; Ding, Z.; Ganem, B.; Creighton, D. J. J. Med. Chem. 2003, 46, 194.
2. (b) Banwell, M. G.; Crasto, C. F.; Easton, C. J.; Karoli, T.; March, D. R.; Nairn, M. R.; O'Hanlon, P. J.; Oldham, M. D.; Willis, A. C.; Yue, W. Chem. Commun. 2001, 2210.
3. (c) Kerr, W. J.; McLaughlin, M.; Pauson, P. L.; Robertson, S. M. J. Organomet. Chem. 2001, 630, 104.
4. (d) Kabat, M. M.; Kiegiel, J.; Cohen, N.; Toth, K.; Wovkulich, P. M.; Uskokovic, M. R. J. Org. Chem. 1996, 61, 118.
5. (e) Wexler, B. A.; Toder, B. H.; Minaskanian, G.; Smith, A. B. III J. Org. Chem. 1982, 47, 3333.
6. (f) Smith, A. B. III; Branca, S. J.; Pilla, N. N.; Guaciaro, M. A. J. Org. Chem. 1982, 47, 1855.
7. (g) Smith, A. B. III; Guaciaro, M. A.; Schow, S. R.; Wovkulich, P. M.; Toder, B. H.; Hall, T. W. J. Am. Chem. Soc. 1981, 103, 219.
8. (a) Guaciaro, M. A.; Wovkulich, P. M.; Smith, A. B. III Tetrahedron Lett. 1978, 4661.
9. (b) Smith, A. B. III; Branca, S. J.; Guaciaro, M. A.; Wovkulich, P. M.; Korn, A. Org. Synth., Coll. Vol. VII; Wiley: New York, 1990, 271.
10. (a) Ito, H.; Hasegawa, M.; Takenaka, Y.; Kobayashi, T.; Iguchi, K. J. Am. Chem. Soc. 2004, 126, 4520.
11. (b) Ito, H.; Konishi, M.; Iguchi, K. Tetrahedron Lett. 2004, 45, 1941.
12. (c) Ito, H.; Kobayashi, T.; Hasegawa, M.; Iguchi, K. Tetrahedron Lett. 2003, 44, 1259.
13. For reviews, see: (a) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
14. (b) Rezgui, F.; Amri, H.; El Gaied, M. M. Tetrahedron 2003, 59, 1369.
15. (c) Iwabuchi, Y.; Hatakeyama, S. J. Synth. Org. Chem., Jpn. 2002, 60, 2.
16. (d) Langer, P. Angew. Chem. Int. Ed. 2000, 39, 3049.
17. (e) Ciganek, E. Org. React. (N.Y.) 1997, 51, 201.
18. (f) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
19. (g) Drewes, S. E.; Roots, G. H. P. Tetrahedron 1988, 44, 4653.
20. (a) Shi, M.; Chen, L.-H. Chem. Commun. 2003, 1310.
21. (b) Zanardi, F.; Appendino, G.; Casiraghi, G. Chemtracts 2002, 15, 490.
22. (c) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
23. (d) Leadbeater, N. E.; van der Pol, C. J. Chem. Soc., Perkin Trans, 1 2001, 2831.
24. (e) Shi, M.; Jiang, J.-K.; Cui, S.-C.; Feng, Y.-S. J. Chem. Soc., Perkin Trans, 1 2001, 390. (
25. f) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
26. (g) Jenner, G. Tetrahedron Lett. 2000, 41, 3091.
27. (h) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489.
28. Yamada, Y. M. A.; Ikegami, S. Tetrahedron Lett. 2000, 41, 2165.
29. (j) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271.
30. (k) Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815.
31. (a) Luo, S.; Zhang, B.; He, J.; Janczuk, A.; Wang, P. G.; Cheng, J.-P. Tetrahedron Lett. 2002, 43, 7369.
32. (b) Gatri, R.; El Gaied, M. M. Tetrahedron Lett. 2002, 43, 7835.
33. (c) Lee, K.-Y.; GowriSankar, S.; Kim, J.-N. Tetrahedron Lett. 2004, 45, 5485.
34. (d) Sugahara, T.; Ogasawara, K. Synlett 1999, 419; see also references 1b and 1d.
35. (a) Rezgui, F.; El Gaied, M. M. Tetrahedron Lett. 1998, 39, 5965.
36. (b) Aggarwal, V. K.; Dean, D. K.; Mereu, A.; Williams, R. J. Org. Chem. 2002, 67, 510.
37. (c) Yadav, V. K.; Senthil, G.; Babu, G.; Parvez, M.; Reid, J. L. J. Org. Chem. 2002, 67, 1109; see also references 6b and 6c.
38. Chong, B.-D.; Ji, Y.-I.; Oh, S.-S.; Yang, J.-D.; Baik, W.; Koo, S. J. Org. Chem. 1997, 62, 9323.