A versatile synthesis of various substituted taurines from vicinal amino alcohols and aziridines

European Journal of Organic Chemistry

Volumn , Issue 33, 2009, Pages 5841-5846

  Chen, Ning ^a   Jia, Weiyi ^a   Xu, Jiaxi ^a  

^a BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

Author keywords

Amino acids; Amino alcohols; Heterocycles; Sulfonic acids; Synthetic methods

Indexed keywords

EID: 72849134310     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900759     Document Type: Article

References (58)

1. For a review, see: J. X. Xu, Chin. J. Org. Chem. 2003, 23, 1-9.
2. For a review, see: R. C. Gupta, T. Win, S. Bittner, Curr. Med. Rev. 2005, 12, 2021-2039.
3. B. Wickberg, Acta Chem. Scand. 1957, 11, 506-511.
4. For a review, see: R. J. Huxtable, Physiol. Rev. 1992, 72, 101-163.
5. M. Satake, Y. Chiba, Y. Kohma, K. Yamamoto, M. Okabe, T. Mimura, T. Imanishi, C. Iwata, Experientia 1989, 45, 1110-1112.
6. a) A. Obreza, S. Gobec, Curr. Med. Rev. 2004, 11, 3263-3278;
7. b) S. M. Liebowitz, J. B. Lombardini, C. I. Allen, Biochem. Pharmacol. 1988, 37, 1303-1309;
8. c) S. M. Liebowitz, J. B. Lombardini, P. S. Salva, Biochem. Pharmacol. 1987, 36, 2109-2114.
9. a) W. J. Moree, G. A. van der Marel, R. M. J. Liskamp, Tetrahedron Lett. 1991, 32, 409-412;
10. b) W. J. Moree, G. A. van der Marel, R. M. J. Liskamp, J. Org. Chem. 1995, 60, 5157-5169;
11. c) D. W. P. Lowik, M. R. M. J. Liskamp, Eur. J. Org. Chem. 2000, 1219-1228;
12. d) C. Giordano, G. Lucente, A. Masi, M. P. Paradisi, A. Sansone, S. Spisani, Bioorg. Med. Chem. 2006, 14, 2642-2652;
13. e) F. D. He, F. H. Meng, X. L. Song, W. X. Hu, J. X. Xu, Org. Lett. 2009, 11, 3922-3925.
14. a) S. Gabriel, H. Ohle, Ber. Dtsch. Chem. Ges. 1917, 50, 804-808;
15. b) P. Rumpf, Bull. Soc. Chim. Fr. 1938, 5, 871-888;
16. c) J. W. Barnett, D. J. Dupre, B. J. Holloway, F. A. Robinson, J. Chem. Soc. 1944, 94-96.
17. a) H. Higashiura, H. Morino, H. Matsuura, Y. Toyomaki, K. Ienaga, J. Chem. Soc. Perkin Trans. 1 1989, 1479-1481;
18. b) D. Braghiroli, M. Di Bella, M. Saladini, Tetrahedron: Asymmetry 1996, 7, 831-836;
19. D. Braghiroli, M. Di Bella, Tetrahedron: Asymmetry 1997, 8, 2209-2213
20. a) P. Rumpf, Bull. Soc. Chim. Fr. 1955, 945-946;
21. b) W. Zhang, B. Y. Wang, N. Chen, D.-M. Du, J. X. Xu, Synthesis 2008, 197-200.
22. a) R. L. Heath, H. A. Piggott, J. Chem. Soc, 1947, 1481-1485;
23. b) M. H. Gold, M. Skebelsky, G. Lang, J. Org. Chem. 1951, 16, 1500-1502.
24. a) K. Higashiura, K. lenaga, J. Org. Chem. 1992, 57, 764-766;
25. b) W. J. Moree, G. A. Van der Marel, R. M. J. Liskamp, Tetrahedron Lett. 1992, 33, 6389-6392;
26. c) M. C. F. Monnee, M. F. Marijne, A. J. Brouwer, R. M. J. Liskamp, Tetrahedron Lett. 2000, 41, 7991-7995;
27. d) J. X. Xu, S. Xu, Synthesis 2004, 276-282;
28. e) B. Y. Wang, W. Zhang, L. L. Zhang, D.-M. Du, G. Liu, J. X. Xu, Eur. J. Org. Chem. 2008, 350-355.
29. F. M. Cordero, M. Cacciarini, F. Machetti, F. De Darlo, Eur. J. Org. Chem. 2002, 1407-1411.
30. a) J. X. Xu, Tetrahedron: Asymmetry 2002, 13, 1129-1134;
31. b) N. Chen, M. Zhu, W. Zhang, D.-M. Du, J. X. Xu, Amino Acids 2009, 37, 309-313.
32. L. B. Hu, H. Zhu, D.-M. Du, J. X. Xu, J. Org. Chem. 2007, 72, 4543-4546.
33. a) J. X. Huang, F. Wang, D.-M. Du, J. X. Xu, Synthesis 2005, 2122-2128;
34. b) J. X. Huang, D.-M. Du, J. X. Xu, Synthesis 2006, 315-319;
35. c) H. Yu, S.-L. Cao, L. L. Zhang, G. Liu, J. X. Xu, Synthesis 2009, 2205-.2209.
36. a) D. Enders, S. Wallert, Synlett 2002, 304-306;
37. b) D. Enders, S. Wallert, J. Runsink, Synthesis 2003, 1856-1868.
38. a) D. Enders, S. Wallert, Tetrahedron Lett. 2002, 43, 5109-5111;
39. b) D. Enders, A. Moll, Synthesis 2005, 1807-1816.
40. D. Enders, D. Iffland, G. Raabe, Synthesis 2009, 1682-1688.
41. S. Ratner, H. T. Clarke, J. Am. Chem. Soc. 1937, 59, 200-206.
42. a) M. G. Ettlinger, J. Am. Chem. Soc. 1950, 72, 4792-.4796;
43. b) H. J. Roth, H. Schlump, Arch. Pharm. 1963, 296, 213-.217;
44. c) Y Nagao, Y. Hagiwara, T. Kumagai, M. Ochiai, T. Inoue, K. Hashimoto, E. Fujita, J. Org. Chem. 1986, 51, 2391-2393;
45. d) R. A. Aitken, D. P. Armstrong, R. H. B. Gait, S. T. E. Mesher, J. Chem. Soc. Perkin Trans. 1 1997, 2139-2146;
46. e) M. M. Al- hamadsheh, N. C. Waters, D. P. Huddler, M. Kreishman-Deitrick, G. Florova, K. A. Reynolds, Bioorg. Med. Chem. Lett. 2007, 17, 879-883;
47. f) A. Osorio-Lozada, H. F. Olivo, Org. Lett. 2008, 10, 617-620.
48. D. Delaunay, L. Toupet, M. Le Corre, J. Org. Chem. 1995, 60, 6604-6607.
49. M. Fujita, Y. Miyashita, N. Amir, Y. Kawamoto, K. Kanamori, K. Okamoto, Polyhedron 2005, 24, 1991-2001.
50. T. A. Foglia, L. M. Gregory, G. Maerker, S. F. Osman, J. Org. Chem. 1971, 36, 1068-1072.
51. The specific rotation of (R)-5-phenylthiazolidine-2-thione (2f′ is unknown. To determine its configuration and optical, purity, it was further oxidized into the known. (R)-1-phenyltaurine (4f′) and compared with the reported data. See the Supporting Information, and also J. X. Xu, N. Chen, Faming Zhuanli Shenqing Gongkai Shuomingshu 2009, CN101337914
52. [Chem. Abstr. 2009, 150, 167868].
53. a.) H. Wenker, J. Am. Chem. Soc 1935, 57, 2328;
54. b) M. Zhu, L. B. Hu, N. Chen, D.-M. Du, J. X. Xu, Lett. Org. Chem. 2008, 5, 212-217.
55. J. Wu, Z. B. Luo, L. X. Dai, X. L. Hou, J. Org. Chem. 2008, 73, 9137-9139.
56. CAUTION! Peribrmic acid is potentially explosive. Although no explosion occurred during our experiments, attention should be paid towards safety.
57. K. Schank, F. Werner, Liebigs Ann. Chem. 1979, 1977-1991.
58. D. H. R. Barton, D. P. Manly, D. A. Widdowson, J. Chem. Soc Perkin Trans. 1 1975, 1568-1574.