Chiral auxiliary-bearing isocyanides as synthons: Synthesis of strongly fluorescent (+)-5-(3,4-dimethoxyphenyl)-4-[[N-[(4S)-2-oxo-4-(phenylmethyl-2-oxazol idinyl]]carbonyl]oxazole and its enantiomer

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8750-8754

  Tang, Jian S ^a   Verkade, John G ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; FLUORESCENCE; QUANTUM CHEMISTRY; REACTION ANALYSIS; TECHNIQUE; X RAY ANALYSIS;

EID: 0030443084     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961554g     Document Type: Article

References (37)

1. Schöllkopf, U. Angew Chem., Int. Ed. Engl. 1977, 16(6), 339.
2. (a) Suzuki, M.; Iwasaki, T.; Miyoshi, M.; Okamuya, K.; Matsumoto, K. J. Org. Chem. 1973, 38(2), 3571.
3. (b) Tang, J. S., Verkade, J. G. J. Org. Chem. 1994, 59, 7793.
4. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857.
5. (a) Christensen, P. L.; Yeung E. S. Anal. Chem. 1989, 61(3), 1345.
6. (b) Yeung, E. S., private communication.
7. (a) Evans, D. A.; Mathre, D. J. J. Org. Chem. 1986, 50(11), 1831.
8. (b) Evans, D. A.; Takes, J. M.; McGee, L. R.; Ennis, M. O.; Mathre, D. J.; Barroli, J. Pure Appl. Chem. 1981, 53, 1109.
9. (c) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeak, M. T. J. Am. Chem. Soc. 1990, 112, 8215.
10. Evans, D. A.; Ennis, M. D.; Le, T. J. Am. Chem. Soc. 1984, 106, 11154.
11. (a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103(8), 2127.
12. (b) Evans, D. A.; Weber, A. G. J. Am. Chem. Soc. 1986, 108, 6757.
13. (c) Evans, D. A.; Rieger, D. C.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1981, 113, 1047.
14. (d) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, U. T.; Sheppard, G. S. J. Am. Chem. Soc. 1980, 112(2), 867.
15. (a) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1980, 112, 4011.
16. (b) Evans, D. A.; Ellman, J. A.; Dorow, R. Tetrahedron Lett. 1987, 28(11), 1123.
17. (a) Evans, D. A.; Britton, T. C. J. Am. Chem. Soc. 1987, 109(22), 6881.
18. (b) Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111(3), 1063.
19. (a) Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am. Chem. Soc. 1986, 108, 6395.
20. (b) Trinable, L. A.; Vederas, J. F. J. Am. Chem. Soc. 1986, 108, 6397.
21. (c) Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F., Jr. Tetrahedron 1988, 44(7), 5525.
22. Evans, D. A.; McCrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1980, 167(14), 4347.
23. (a) Evans, D. A.; Chapman, K. T.; Bisaka, J. Tetrahedron Lett. 1984, 25(37), 4071.
24. (b) Evans, D. A.; Chapman, K. T.; Bisaka, J. J. Am. Chem. Soc. 1984, 106, 4363.
25. Chem. Eng. News 1993, Apr 19, p 4; Oct 11, p 2; Dec 13 p 4.
26. Chem. Eng. News 1993, Apr 19, p 4; Oct 11, p 2; Dec 13 p 4.
27. Chem. Eng. News 1993, Apr 19, p 4; Oct 11, p 2; Dec 13 p 4.
28. Ugi, J.; Fetzer, U.; Eholzer, U.; Knupfer, H.; Offermann, K. Angew. Chem., Int. Ed. Engl. 1965, 4(6), 472.
29. Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26-(9), 894.
30. Hoppe, I.; Scholkopf, U. Chem. Rev. 1976, 109, 482.
31. Tang, J. S.; Verkade, J. G. Tetrahedron Lett. 1993, 34(18), 2903.
32. Muramatsu, I.; Murakami, H.; Yoneda, T.; Hagitani, A. Bull. Chem. Soc. Jpn. 1965, 38(2), 244.
33. Birlman, I. B., Ed. Handbook of Fluorescence Spectra of Aromatic Molecules, 2nd ed.; Academic Press: New York, 1971; pp 291 and 306.
34. Parker, C. A.; Rees, W. T. Analyst 1961, 85, 587.
35. Reichardt, C. Ed. Solvent Effects in Organic Chemistry; Verlag Chemie, Weinheim, New York, 1979.
36. SHELXTL-Plus, Siemens Analtical X-ray Inc., Madison, WI.
37. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.