Novel synthesis of ynolates via the cleavage of ester dianions: α-bromo and α,α-dibromo esters as precursors

Tetrahedron

Volumn 54, Issue 11, 1998, Pages 2411-2422

  Shindo, Mitsuru ^a   Sato, Yusuke ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMIDE; ANION; BROMINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER; HALOGEN; LACTONE; LITHIUM;

ARTICLE; CHEMICAL REACTION; INORGANIC CHEMISTRY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032510257     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00006-4     Document Type: Article

References (40)

1. 1. (a) House, H. O. Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin, Inc.: California, 1972; p 492-628.
2. (b) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 99-319.
3. 2. (a) Schöllkopf, U.; Hoppe, I. Angew. Chem. Int. Ed. Engl. 1975, 14, 765.
4. (b) Hoppe, I.; Schöllkopf, U. Liebigs Ann. Chem. 1979, 219-226.
5. 3. (a) Woodbury, R. P.; Long, N. R. Rathke, M. W. J. Org. Chem. 1978, 43, 376. See also;
6. (b) Kita, Y.; Tsuzuki, Y.; Kitagaki, S.; Akai, S. Chem. Pharm. Bull., 1994, 42, 233-236.
7. (c) Akai, S.; Kitagaki, S.; Naka, T.; Yamamoto, K.; Tsuzuki, Y.; Matsumoto, K.; Kita, Y. J. Chem. Soc., Perkin Trans. 1, 1996, 1705-1709.
8. 4. (a) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 7321-7323.
9. (b) Kowalski, C. J.; Haque, M. S.; Fields, L. W. J. Am. Chem. Soc. 1985, 107, 1429-1430.
10. (c) Kowalski, C. J.; Haque, M. S. J. Org. Chem. 1985, 50, 5140-5142.
11. (d) Kowalski, C. J.; Lal, G. S. Tetrahedron Lett. 1987, 28, 2463-2466.
12. (e) Kowalski, C. J.; Reddy, R. E. J. Org. Chem. 1992, 57, 7194-7208.
13. (f) Reddy, R. E.; Kowalski, C. J. Org. Synth. 1993, 71, 146. Satoh and Yamakawa reported a similar method using α-chloro α-sulfinyl ketones:
14. (g) Satoh, T.; Mizu, Y.; Hayashi, Y.; Yamakawa, K. Tetrahedron Lett. 1994, 35 133-134.
15. 5. Stang, P. J.; Roberts, K. A. J. Am. Chem. Soc. 1986, 108, 7125-7127.
16. 6. Julia, M.; Saint-Jalmes, V. P.; Verpeaux, J. N. Synlett 1993, 233-234.
17. 7. Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634-7635.
18. 8. Adlington, R. M.; Barrett, A. G. M.; Quayle, P.; Walker, A. J. Chem. Soc., Chem. Comm. 1981, 404-405.
19. 9. (a) Kowalski, C. J.; Haque, M. S. J. Am. Chem. Soc. 1986, 108, 1325-1327.
20. (b) Kowalski, C. J.; Lal, G. S. J. Am. Chem. Soc. 1986, 108, 5356-5357.
21. 10. Shindo, M. Tetrahedron Lett. 1997, 38, 4433-4436.
22. 11. (a) Sullivan, D. F.; Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1977, 42, 2038-2039.
23. (b) Haner, R.; Laube, T.; Seebach, D. J. Am. Chem. Soc. 1985, 107, 5396-5403. In this article, the authors described that addition of alkyllithium to monosubsituted ketenes generated from ester enolates was unsuccessful because ynolates might be formed.
24. (c) Tomioka, K.; Shindo, M.; Koga, K. J. Org. Chem. 1990, 55, 2276-2277.
25. (d) For zinc enolate: Pratt, R. F.; Bruice, T. C. J. Am. Chem. Soc. 1970, 92, 5956-5964.
26. 12. (a) Lau, K. S. Y.; Schlosser, M. J. Org. Chem. 1978, 43, 1595-1598.
27. (b) Schlosser, M.; Wei, H.-x. Tetrahedron 1997, 53, 1735-1742.
28. 13. Kowalski, C. J.; Lal, G. S.; Haque, M. S. J. Am. Chem. Soc. 1986, 108, 7127-7128.
29. 14. The aggregation and its effect on reactivity of lithium amides and lithium halides is being examined in detail; see: Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1994 116, 9198-9202 and references cited therein.
30. 13C-NMR spectra, but their relative configurations have not been determined.
31. 16. (a) Danheiser, R. L.; Nowick, J. S. J. Org. Chem. 1991, 56, 1176-1185. For reviews of the chemistry of β-lactones, see:
32. (b) Pons, J.-M.; Pommier, A. Synthesis 1993, 441-459.
33. (c) Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, p 342-350.
34. 17. Mulzer, J.; Chucholowski, A. Angew. Chem. Int. Ed. Engl. 1982, 21, 777-778.
35. 18. Mulzer, J.; Kerkmann, T. J. Am. Chem. Soc. 1980, 102, 3620-3622.
36. 19. The relative configuration of 8a is the same as that of one of the β-lactone isomers (6), but those of 8b and 8c were determined by NOE of the corresponding olefin via decarboxylation.
37. 20. Schick, H.; Ludwig, R.; Kleiner, K.; Kunath, A. Tetrahedron 1995, 51, 2939-2946.
38. 21. Berry, J. P.; Isbell, A. F.; Hunt, G. E. J. Org. Chem. 1972, 37, 4396-4399.
39. 22. Kawahara, S.; Kawakami, H. Yakugaku Zasshi 1961, 81, 1057-1 1062.
40. 23. Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281-5284.