New synthesis of Evans chiral oxazolidinones by using Sharpless AA reaction

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 11, 1998, Pages 1753-1754

  Li, Guigen ^a   Lenington, Robert ^a   Willis, Steven ^a   Kim, Sun Hee ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748614120     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a801404c     Document Type: Article

References (26)

1. D. J. Ager, I. Prakash and D. Schaad, Aldrichimica Acta, 1997, 30, 3.
2. D. A. Evans, J. Bartroli and T. L. Shih, J. Am. Chem. Soc., 1981, 103, 2127.
3. (a) D. A. Evans, K. T. Chapman, D. T. Hung and A. T. Hawaguchi, Angew. Chem., Int. Ed. Engl., 1987, 26, 1184;
4. (b) I. W. Davies, C. H. Senanayake, L. Castonguay, R. D. Larsen, T. R. Verhoeven and P. J. Reider, Tetrahedron Lett., 1995, 36, 7619.
5. M. A. Walker and C. H. Heathcock, J. Org. Chem., 1991, 56, 5747.
6. (a) D. A. Evans, M. T. Bilodeau, T. Somers, J. Clardy, D. Cherry and Y. Kato, J. Org. Chem., 1991, 56, 5750;
7. (b) G. Li, K. C. Russell, M. A. Jarosinski and V. J. Hruby, Tetrahedron Lett., 1993, 34, 2565.
8. (a) J. R. Cage and D. A. Evans, Org. Synth., 1990, 68, 77;
9. (b) M. Sudharshan and P. G. Hultin, Synlett, 1997, 2, 171.
10. (a) W. Lubell and H. Rapoport, J. Org. Chem., 1989, 54, 3824;
11. (b) T. P. Curren, M. P. Pollastri, S. M. Ablelleira, R. J. Messier, T. A. McCollum and C. G. Rowe, Tetrahedron Lett., 1994, 35, 5409.
12. S. Iwama and S. Katsumura, Bull. Chem. Soc. Jpn., 1994, 67, 3363.
13. J. Takacs, M. R. Jaber and A. S. Vellekoop, Abstracts of Papers, 214th ACS National Meeting, Las Vegas, September 7th-11th, 1997, ORG 206.
14. D. Xu and K. B. Sharpless, Tetrahedron, 1993, 34, 951.
15. J. D. Bias, J. C. Carretero and E. Domingurez, Tetrahedron Lett., 1994, 35, 4603.
16. E. Nicolas, K. C. Russell and V. J. Hruby, J. Org. Chem., 1993, 58, 766.
17. A. K. Ghosh and W. Liu, J. Org. Chem., 1996, 61, 6175.
18. M. P. Sibi, D. Rutherford and R. Sharma, J. Chem. Soc., Perkin Trans. 1, 1994, 1675.
19. (a) G. Li, H.-T. Chang and K. B. Sharpless, Angew. Chem., Int. Ed. Engl., 1996, 35, 451;
20. (b) J. Rudolph, P. C. Sennhenn, C. P. Vlaar and K. B. Sharpless, Angew. Chem., Int. Ed. Engl., 1996, 35, 2810.
21. G. Li, H. H. Angert and K. B. Sharpless, Angew. Chem., Int. Ed. Engl., 1996, 35, 2813.
22. -1]: 12.98 min (3, S), 12.18 min(5, R); 21.97 min (9, S), 26.91 min (10, R).
23. N. Lewis, A. McKillop, R. J. K. Taylor and R. J. Watson, Synth. Commun., 1995, 25, 561.
24. -1, 8.44 min (S), 10.70 min (R). The enantiomeric excesses of benzyl carbamate-based AA products (2, 4, 7 and 9) were determined by using the HPLC conditions as described in ref. 16.
25. 3 (10 mol%) and gave a lower yield of 82%.
26. 99% ee indicates that only one enantiomer was observed in HPLC analysis.