3-Unsubstituted 1,5-diaryl-2,4-pentanediones and -4-methoxy-2-pentanones: Synthesis via corresponding 3-hydroxy ketones generated from 2-isoxazolines

Journal of Organic Chemistry

Volumn 61, Issue 24, 1996, Pages 8604-8609

  Pulkkinen, Juha T ^a   Vepsäläinen, Jouko J ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANONE; DIKETONE; KETONE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029959623     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960887a     Document Type: Article

References (31)

1. Bonati, F. Organomet. Chem. Rev. 1966, 1, 379.
2. Pike, R. M. Coord. Chem. Rev. 1967, 2, 163.
3. (a) Alberts, A. H.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1976, 958.
4. (b) Maverik, A. W.; Buckingham, S. C.; Yao, Q.; Bradbury, J. R.; Stanldy, G. G. J. Am. Chem. Soc. 1986, 108, 7430.
5. (c) Kobuke, Y.; Satoh, Y. J. Am. Chem. Soc. 1992, 114, 789.
6. (d) Kobuke, Y.; Kokubo, K.; Munakata, M. J. Am. Chem. Soc. 1995, 117, 12751.
7. (a) Dashkevich, L. B.; Boksiner, E. I. Zh. Obshch. Khim. 1958, 28, 2845.
8. (b) Dashkevich, L. B.; Kuzmenkov, L. N. Zh. Obshch. Khim. 1959, 29, 2367.
9. (c) Bryant, D. R.; Hauser, C. R. J. Org. Chem. 1961, 27, 694.
10. (d) Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360.
11. (a) Hauser, C. R.; Swamer, F. W.; Adams, J. T. Org. React. 1954, 8, 59.
12. (b) Hause, H. O. Modern Synthetic Reactions; 2nd ed.; Benjamin: Menlo Park, CA, 1972; pp 629-682.
13. (a) Casnati, G.; Quilico, A.; Ricca, A.; Vita Finzi, P. Tetrahedron Lett. 1966, 7, 233.
14. (b) Bast, K.; Christl, M.; Huisgen, R.; Mack, W.; Sustmann, R. Chem. Ber. 1973, 106, 3258.
15. (c) Baraldi, P. G.; Barco, A.; Benetti, S; Pollini, G. P.; Simoni, D. Synthesis 1987, 857.
16. (d) Bianchi, G.; De Amici, M. J. Chem. Soc., Chem. Commun. 1978, 962.
17. (a) Nielsen, A. T.; Houlihan, W, J. Org. React. 1968, 16, 1.
18. (b) Mukaiyama, T. Org. React. 1982, 28, 203.
19. (a) Lee, G. A. Synthesis 1982, 508.
20. (b) Ko, S. S.; Confalone, P. N. Tetrahedron 1985, 41, 3511.
21. (c) Sugiyama, T. Appl. Organomet. Chem. 1995, 9, 399.
22. (d) Mancera, M.; Roffé, I.; Galbis, J. A. Tetrahedron 1995, 51, 6349.
23. (a) Curran, D. P. J. Am. Chem. Soc. 1982, 104, 4024.
24. (b) Kozikowski, A. P.; Adamczyk, M. Tetrahedron Lett. 1982, 23, 3123.
25. Pulkkinen, J.; Vepsäläinen, J.; Laatikainen, R. Tetrahedron Lett. 1994, 35, 9749.
26. (a) Katayama, S.; Fukuda, K.; Watanabe, T.; Yamauchi, M. Synthesis 1988, 178.
27. (b) Katayama, S.; Watanabe, T.; Yamauchi, M. Chem. Pharm. Bull. 1990, 38, 3314.
28. Corey, E. J.; Kim, C. U. J. Am. Chem. Soc. 1972, 94, 7586.
29. Brown, H. C.; Subba Rao, B. C. J. Am. Chem. Soc. 1958, 80, 5377.
30. White, W. N.; Gwynn, D.; Schlitt, R.; Girard, C.; Fife, W J. Am. Chem. Soc. 1958, 80, 3271.
31. Vyas, G. N.; Shah, N. M. Organic Syntheses; Wiley: New York, Coll. Vol. 4, 1963; p 836.