Cesium (Z)-2-carbomethoxyethenethiolate: A reagent for the preparation of (Z)-2-carbomethoxyethenyl thioethers including selected cysteine and homocysteine derivatives

European Journal of Organic Chemistry

Volumn , Issue 4, 2009, Pages 547-553

  O'Donnell, Jennifer S ^a   Singh, Suneel P ^a   Metcalf, Thomas A ^a   Schwan, Adrian L ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

Amino acids; Cesium; Sulfur; Synthetic methods

Indexed keywords

EID: 60849133887     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200801025     Document Type: Article

References (45)

1. A. A. Esmaili, M. Ghereghloo, M. R. Islami, H. R. Bijanzadeh, Tetrahedron 2003, 59, 4785-4788.
2. V. A. Bakulev, V. S. Berseneva, N. P. Belskaia, Y. Y. Morzherin, A. Zaitsev, W. Dehaen, I. Luyten, S. Toppet, Org. Biomol. Chem. 2003, 1, 134-139.
3. M. Journet, A. Rouillard, D. Cai, R. D. Larsen, J. Org. Chem. 1997, 62, 8630-8631.
4. M. Mitsukuchi, T. Ikemoto, M. Taguchi, S. Higuchi, S. Abe, H. Yasui, K. Hatayama, K. Sota, Chem. Pharm. Bull. 1989, 37, 3286-3293.
5. N. Maezaki, S. Yagi, R. Yoshigami, J. Maeda, T. Suzuki, S. Ohsawa, K. Tsukamoto, T. Tanaka, J. Org. Chem. 2003, 68, 5550-5558.
6. Y. V. Bilokin, A. Melman, V. Niddam, B. Benhamu, M. D. Bachi, Tetrahedron 2000, 56, 3425-3437.
7. J. Zhang, S. Saito, T. Koizumi, J. Org. Chem. 1998, 63, 9375-9384.
8. L. N. Sobenina, A. P. Demenev, A. b. I. Mikhaleva, V. N. Elokhina, A. G. Mal'kina, O. g. A. Tarasova, I. A. Ushakov, B. A. Trofimov, Synthesis 2001, 293-299.
9. Y. Arai, Y. Hayashi, M. Yamamoto, H. Takayema, T. Koizumi, J. Chem. Soc. Perkin Trans. 1 1988, 3133-3140.
10. O. De Lucchi, M. Buso, G. Modena, Tetrahedron Lett. 1987, 28, 107-110.
11. G. T. Crisp, M. J. Millan, Tetrahedron 1998, 54, 637-648.
12. P. D. Halphen, T. C. Owen, J. Org. Chem. 1973, 38, 3507-3510.
13. M. E. Jung, K. R. Buszek, J. Am. Chem. Soc. 1988, 110, 3965-3969.
14. A. L. Schwan, R. R. Strickler, Y. Lear, M. L. Kalin, T. E. Rietveld, T.-J. Xiang, D. Brillon, J. Org. Chem. 1998, 63, 7825-7832.
15. J. S. O'Donnell, A. L. Schwan, Tetrahedron Lett. 2003, 44, 6293-6296.
16. H. R. Pfaendler, J. Gosteli, R. B. Woodward, J. Am. Chem. Soc. 1980, 102, 2039-2043.
17. H. R. Pfaendler, J. Gosteli, R. B. Woodward, J. Am. Chem. Soc. 1979, 101, 6306-6310.
18. P. H. Crackett, C. W. Greengrass, R. J. Stoodley, Tetrahedron Lett. 1986, 27, 1301-1304.
19. N. D. Pearson, T. C. Smale, R. Southgate, Tetrahedron Lett. 1995, 36, 4493-4496.
20. Under IUPAC nomenclature, the targets (products) of this chemistry are known as methyl (2Z)-3-(alkylsulfanyl)prop-2-enoates.
21. N. D. Smith, M. Goodman, Org. Lett. 2003, 5, 1035-1037.
22. C. Dugave, A. Menez, J. Org. Chem. 1996, 61, 6067-6070.
23. O. Arjona, R. Medel, J. Rojas, A. M. Costa, J. Vilarrasa, Tetrahedron Lett. 2003, 44, 6369-6373.
24. J. S. O'Donnell, PhD Thesis, University of Guelph, 2005.
25. M. Hashemi, M. Akhbari, S. Arianfar, J. Sulfur Chem. 2004, 25, 95-99.
26. For more examples of ethenethiolate chemistry, see: a) M. Ochiai, M. Hirobe, K. Miyamoto, J. Am. Chem. Soc. 2006, 128, 9046-9047;
27. b) A. L. Schwan, M. D. Refvik, Synlett 1998,96-98;
28. c) V. A. Potapov, N. K. Gusarova, B. A. Trofimov, S. V. Amosova, A. S. Kashik, Sulfur Lett. 1985, 3, 151-154;
29. d) K. Kpegba, P. Metzner, Tetrahedron Lett. 1990, 31, 1853-1856;
30. e) E. Block, S.-H. Zhao, J. Org. Chem. 1992, 57, 5815-5817;
31. f) S. V. Amosova, G. M. Gavrilova, A. V. Afonin, Russ.J. Org. Chem. 2005, 41,402-405.
32. H. Shao, S. H. H. Wang, C.-W. Lee, G. Oesapay, M. Goodman, J. Chem. Soc. 1995, 60, 2956-2957.
33. C. Dugave, A. Menez, Tetrahedron: Asymmetry 1997, 8, 1453-1465.
34. R. N. Salvatore, R. A. Smith, A. K. Nischwitz, T. Gavin, Tetrahedron Lett. 2005, 46, 8931-8935.
35. Silver (Z)-carbomethoxyethenethiolate is also known, but its preparation also requires hydroxide. M. Giffard, I. Léauté, J. Chem. Res. (S) 1990, 320-321.
36. L. N. Owen, M. U. S. Sultanbawa, J. Chem. Soc. 1949, 3109-3113.
37. W. H. Mueller, J. Org. Chem. 1966, 31, 3075-3079.
38. G. Dallas, J. W. Lown, J. C. N. Ma, J. Chem. Soc. C 1968, 2510-2514.
39. D. T. Witiak, M. C. Lu, J. Org. Chem. 1968, 33, 4451-4454.
40. The separability of 7 from its E isomer is important, as in our experience, the chromatographic separation of E/Z isomers of alkyl carbomethoxyethenyl thioethers can be challenging.
41. X. Moreau, J.-M. Campagne, J. Org. Chem. 2003, 68, 5346-5350.
42. C. P. Sar, J. Jeko, P. Fajer, K. Hideg, Synthesis 1999, 1039-1045.
43. G. T. Crisp, M. J. Millan, Tetrahedron 1998, 54, 649-666.
44. J. L. Adams, T. M. Chen, B. W. Metcalf, J. Org. Chem. 1985, 50, 2730-2736.
45. U. Koelle, C. Rietmann, J. Tjoe, T. Wagner, U. Englert, Organometallics 1995, 14, 703-713.