A convenient preparation of N-(2-alkynoyl) derivatives of chiral oxazolidin-2-ones and bornane-10,2-sultam

Tetrahedron Asymmetry

Volumn 8, Issue 10, 1997, Pages 1685-1691

  Fonquerna, Sílvia ^a   Moyano, Albert ^a   Pericàs, Miquel A ^a   Riera, Antoni ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BORNANE DERIVATIVE; LITHIUM CHLORIDE; LITHIUM SALT; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 0030914116     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00167-5     Document Type: Article

References (36)

1. (a) Kagan, H. B. Asymmetric Synthesis. Fundamentals and Applications; Thieme: Stuttgart, 1996.
2. (b) Atkinson, R.S. Stereoselective Synthesis; Wiley: New York, 1995.
3. (c) Nogradi, M. Stereoselective Synthesis: A Practical approach, 2nd Ed.; VCH: New York, 1995.
4. (a) Evans, D. A.; Bartrolí, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.
5. (b) Evans, D. A.; Takacs, J. M.; McGee, L. R.; Ennis, M. D.; Mathre, D. J.; Bartrolí, J. Pure & Appl. Chem. 1981, 53, 1109.
6. (c) Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739.
7. (d) Evans, D. A.; Ennis, M. D.; Le, T. J. J. Am. Chem. Soc. 1984, 106, 1154-1156.
8. (a) Oppolzer, W.; Chapuis, G.; Bernardelli, G. Helv. Chim. Acta 1984, 67, 1397-1401.
9. (b) Oppolzer, W. Tetrahedron 1987, 43, 1969-2004.
10. (c) Oppolzer, W.; Barras, J. P. Helv. Chim. Acta 1987, 70, 1666-1675.
11. (d) Oppolzer, W.; Blagg, J.; Rodríguez, I.; Walther, E. J. Am. Chem. Soc. 1990, 112, 2767-2772.
12. For recent references, see:(a) Cantrill, A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. Chem. Commun. 1996, 2631-2632.
13. (b) Sibi, M. P.; Lu, J.; Talbacka, C. L. J. Org. Chem. 1996, 61, 7848-7855.
14. (c) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063-3064.
15. (d) Wipf, P.; Takahashi, H. Chem. Commun. 1996, 2675-2676.
16. (e) Oppolzer, W.; Rosset, S.; De Brabander, J. Tetrahedron Lett. 1997, 38, 1539-1540.
17. (a) Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E. Tetrahedron: Asymmetry 1994, 5, 307-310.
18. (b) Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A.; Bernardes, V.; Greene, A. E.; Alvarez-Larena, A.; Piniella, J. F. J. Am. Chem. Soc. 1994, 116, 2153-2154.
19. (c) Fonquerna, S.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1995, 51, 4239-4254.
20. (d) Bernardes, V.; Kann, N.; Riera, A.; Moyano, A.; Pericàs, M. A.; Greene, A. E. J. Org. Chem. 1995, 60, 6670-6671.
21. (e) Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E.; Alvarez-Larena, A.; Piniella, J. F. J. Org. Chem. 1996, 61, 9016-9020.
22. (f) Torino, J.; Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1996, 52, 14021-14040.
23. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256.
24. Gage, J. R.; Evans, D. A. Org. Synth. 1989, 68, 83-90.
25. Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 154-157.
26. (a) Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111, 1063-1072.
27. (b) Garner, P.; Ho, W. B.; Shim, H. J. Am. Chem. Soc. 1993, 115, 10742-10753.
28. Holzapfel, C.; Pettit, G. R. J. Org. Chem. 1985, 50, 2323-2327.
29. Lee, J. Y.; Chung, Y. J.; Kim, B. H. Synlett 1994, 197-198.
30. Ho, G.-J.; Mathre, D. J. J. Org. Chem. 1995, 60, 2271-2273.
31. Coppola, G. M.; Damon, R. E. Synth. Commun. 1993, 23, 2003-2010.
32. Fonquerna, S.; Moyano, A; Pericàs, M. A.; Riera, A., submitted for publication.
33. (a) Palomo, C.; Berrée, F.; Linden, A.; Villalgordo, J. M. J. Chem. Soc., Chem. Commun. 1994, 1961-1962.
34. (b) Kouklovsky, C.; Pouilhes, A.; Langlois, Y. J. Am. Chem. Soc. 1990, 112, 6672-6679.
35. (a) Herneling, D.; Schäfer, H. J. Chem. Ber. 1988, 121, 1151-1158.
36. (b) Ichikizaki, I.; Yao, C-C.; Fujiya, Y.; Hasebe, Y. Bull. Chem. Soc. Jpn 1955, 28, 80-83.