A mild and convenient procedure for desulfinylation of p-toluenesulfinyl amines

Synlett

Volumn , Issue 3, 2005, Pages 535-537

  Li, Bin Feng ^a   Yuan, Ke ^a   Dai, Li Xin ^a   Hou, Xue Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Amine; Desulfinylation; Lewis acid catalyst; Sulfinamide

Indexed keywords

4 TOLUENESULFINYLAMINE DERIVATIVE; SULFINAMIDE; THIOPHENOL; UNCLASSIFIED DRUG; ZINC CHLORIDE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

EID: 14644445130     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-862352     Document Type: Article

References (27)

1. (a) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13.
2. (b) Zhou, P.; Chen, B. C.; Davis, F. A. Tetrahedron 2004, 60, 8003.
3. Fanelli, D. L.; Szewczyk, J. M.; Zhang, Y. L.; Reddy, G. V.; Burns, D. M.; Davis, F. A. Org. Synth. 2000, 77, 50.
4. For some examples see: (a) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y.-H. J. Org. Chem. 1996, 61, 440.
5. (b) Mikolajczyk, M.; Lyzwa, P.; Drabowicz, J.; Wieczorek, M. W.; Blaszczyk, J. Chem. Commun. 1996, 1503.
6. (c) Lefebvre, I. M.; Evans, S. A. Jr. J. Org. Chem. 1997, 62, 7532.
7. (d) Davis, F. A.; Andemichael, Y. W. Tetrahedron Lett. 1997, 37, 3099.
8. (e) Davis, F. A.; Srirajan, V.; Titus, D. D. J. Org. Chem. 1999, 64, 6931.
9. (f) Davis, F. A.; Lee, S.; Zhang, H. M.; Fanelli, D. L. J. Org. Chem, 2000, 65, 8704.
10. (g) Koriyama, Y.; Nozawa, A.; Hayakawa, R.; Shimizu, M. Tetrahedron 2002, 58, 9621.
11. (h) Aggarwal, V. K.; Castro, A. M. M.; Mereu, A.; Adams, H. Tetrahedron Lett. 2002, 43, 1577.
12. (i) Davis, F. A.; Yang, B. Org. Lett. 2003, 5, 5011.
13. (j) Viso, A.; Delapradilla, R. F.; García, A.; Guerrerostrachan, C.; Alonso, A.; Tortosa, M.; Flores, A.; Martínez-Ripoll, M.; Fonseca, I.; André, I.; Rodríguez, A. Chem.-Eur. J. 2003, 9, 2867.
14. (a) Li, B. F.; Zhang, M. J.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2002, 67, 2902.
15. (b) Li, B. F.; Yuan, K.; Zhang, M. J.; Wu, H.; Dai, L. X.; Wang, Q. R.; Hou, X. L. J. Org. Chem. 2003, 68, 6264.
16. Hua, D. H.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4.
17. Harmata, M.; Kahraman, M.; Jones, D. E.; Pavri, N.; Weatherwax, S. E. Tetrahedron 1998, 54, 9995.
18. Davis, F. A.; Ramachandar, T.; Liu, H. Org. Lett. 2004, 6, 3393.
19. (a) Wang, D. K.; Zhou, Y. G.; Tang, Y.; Hou, X. L.; Dai, L. X. J. Org. Chem. 1999, 64, 4233.
20. (b) Yang, X. F.; Zhang, M. J.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2002, 67, 8097.
21. (c) Wu, J.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2000, 65, 1344.
22. (d) Wu, J.; Hou, X. L.; Dai, L. X. J. Chem. Soc., Perkin Trans. 1 2001, 1314.
23. (e) Fan, R. H.; Zhou, Y. G.; Zhang, W. X.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2004, 69, 335.
24. (f) Fan, R. H.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2004, 69, 689.
25. (g) Ding, C. H.; Dai, L. X.; Hou, X. L. Synlett 2004, 1691.
26. 3S: C, 61.53; H, 5.47; N, 12.66. Found: C, 61.27; H, 5.68; N, 12.51.
27. The ee value of product 2d determined by HPLC was the same as that of α-methylbenzylamine used as starting material to prepare p-toluenesulfinyl amine (1d).