Synthesis of enantiopure tert-butanesulfinamide from tert- butanesulfinyloxazolidinone

Journal of Organic Chemistry

Volumn 69, Issue 24, 2004, Pages 8533-8536

  Qin, Yong ^a   Wang, Canhui ^b   Huang, Zhiyan ^a   Xiao, Xue ^a   Jiang, Yaozhong ^b  

^a SICHUAN UNIVERSITY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINES; AMMONIA; BUTANE; COMPLEXATION; HYDROLYSIS; LITHIUM COMPOUNDS; MAGNESIUM COMPOUNDS; NEGATIVE IONS; REACTION KINETICS;

ENANTIOMERS; ENANTIOPURITY; LIQUID AMMONIA; TERT-BUTANESULFINAMIDE;

SYNTHESIS (CHEMICAL);

AMMONIA; ANION; BIPHENYL DERIVATIVE; BUTANE; ETHANOLAMINE DERIVATIVE; LITHIUM DERIVATIVE; MAGNESIUM DERIVATIVE; OXAZOLIDINONE DERIVATIVE; SULFINAMIDE; TERT BUTANESULFINAMIDE; TERT BUTANESULFINYLOXAZOLIDINONE; TERT BUTYLSULFINYL 4,5 DIPHENYL 1,3 OXAZOLIDINONE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; HYDROLYSIS; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 9344248076     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048576k     Document Type: Article

References (25)

1. Liu, G.-Ch.; Cogan, D. A.; Ellman, J. A. J. Am. Soc. Chem. 1997, 119, 9913.
2. For a recent review on tert-butylsulfinyl imine addition, see: Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
3. For a review of uncovered literatures, see: (a) Jacobsen, M. F.; Skrydstrup, T. J. Org. Chem. 2003, 68, 7122.
4. (b) Ellman, J. A.; McMahon, J. P. Org. Lett. 2004, 6, 1645.
5. (c) Kells, K. W.; Chong, J. M. Org. Lett. 2003, 5, 4215.
6. (d) Evans, J. W.; Ellman, J. A. J. Org. Chem. 2003, 68, 9948.
7. (e) Prakash, G. K. S.; Mandal, M. J. Am. Soc. Chem. 2002, 124, 6538.
8. (a) Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Soc. Chem. 2003, 125, 11276.
9. (b) Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Soc. Chem. 2002, 124, 6518.
10. Backes, B. J.; Dragoli, D. R.; Ellman, J. A. J. Org. Chem. 1999, 64, 5472.
11. (a) Owens, T. D.; Souers, A. J.; Ellman, J. A. J. Org. Chem. 2003, 68, 3.
12. (b) Owens, T. D.; Hollander, F. J.; Oliver, A. G.; Ellman, J. A. J. Am. Soc. Chem. 2001, 123, 1539.
13. (a) Schenkel L. B.; Ellman, J. A. J. Org. Chem. 2004, 69, 1800.
14. (b) Schenkel, L. B.; Ellman, J. A. Org. Lett. 2003, 5, 545.
15. (a) Cogan, D. A.; Liu, G.-Ch.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Soc. Chem. 1998, 120, 8011.
16. (b) Blum, S. A.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2003, 68, 150.
17. (c) Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317.
18. Optically pure tert-butanethiosulfinate prepared by chiral inclusion resolution with BINOL was reported by: Liao, J.; Sun, X.-X.; Cui, X.; Yu, K.-B.; Zhu, J.; Deng, J.-G. Chem. Eur. J. 2003, 9, 2611.
19. Han, Zh.-X.; Krishnamurthy, D.; Grover, P.; Fang, Q. K.; Senanayake, Ch. H. J. Am. Soc. Chem. 2002, 124, 7880.
20. (a) Garcia-Ruano, J. L.; Alonso, R.; Zarzuelo, M. M.; Noheda, P. Tetrahydron: Asymmetry 1995, 6, 1133.
21. (b) The tert-butylsulfinyl-4-phenyl-1,3-oxazolidinone was prepared by Evans; see: Evans, D. A.; Faul, M. M.; Colombo, L.; Bisaha, J. J.; Clardy, J.; Cherry, D. J. Am. Soc. Chem. 1992, 114, 5977.
22. Garcia-Ruano, J. L.; Alemparte, C.; Aranda, M. T.; Zarzuelo, M. M. Org. Lett. 2003, 5, 75.
23. 3 in yields of 93% (1a), 97% (1b), 94% (1c), and 99% (1d), respectively.
24. Wudl, F.; Lee, T. B. K. J. Am. Chem. Soc. 1973, 95, 6349.
25. The cleavage of noncyclic N-acyl-tert-butylsulfinamide sometimes was not successful; see ref 4.