Enantiodivergent, catalytic asymmetric synthesis of γ-amino vinyl sulfones

Journal of Organic Chemistry

Volumn 68, Issue 13, 2003, Pages 5075-5083

  Picó, Anna ^a   Moyano, Albert ^a   Pericàs, Miquel A ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIODIVERGENT SYNTHESIS;

AMINO ACIDS; CATALYSIS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

KETONES;

ALKANEDIOL DERIVATIVE; ALPHA AMINO ACID; CYSTEINE PROTEINASE INHIBITOR; N BUTYLOXYCARBONYL GAMMA AMINOVINYL SULFONE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENZYME INHIBITION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0038209721     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0268456     Document Type: Article

References (49)

1. For recent reviews on cysteine proteases and their inhibitors, see: (a) Otto, H. H.; Schirmeister, T. Chem. Rev. 1997, 97, 133-171. (b) Lecaille, F.; Kaleta, J.; Brömme, D. Chem. Rev. 2002, 102, 4459-4488. (c) Powers, J. C.; Asgian, J. L.; Ekici, Ö. D.; James, K. E. Chem. Rev. 2002, 102, 4639-4750.
2. For recent reviews on cysteine proteases and their inhibitors, see: (a) Otto, H. H.; Schirmeister, T. Chem. Rev. 1997, 97, 133-171. (b) Lecaille, F.; Kaleta, J.; Brömme, D. Chem. Rev. 2002, 102, 4459-4488. (c) Powers, J. C.; Asgian, J. L.; Ekici, Ö. D.; James, K. E. Chem. Rev. 2002, 102, 4639-4750.
3. For recent reviews on cysteine proteases and their inhibitors, see: (a) Otto, H. H.; Schirmeister, T. Chem. Rev. 1997, 97, 133-171. (b) Lecaille, F.; Kaleta, J.; Brömme, D. Chem. Rev. 2002, 102, 4459-4488. (c) Powers, J. C.; Asgian, J. L.; Ekici, Ö. D.; James, K. E. Chem. Rev. 2002, 102, 4639-4750.
4. Robertson, C. D.; Combs, G. H.; North, M.; Mottram, J. C. In Perspectives in Drug Discovery and Design; Anderson, P. S., Kenyon, G. L., Marshall, G. R., Eds.; ESCOM Science: Leiden, 1996; Vol. 6, p 99.
5. (a) Palmer, J. T.; Rasnick, D.; Klaus, J. L.; Brömme, D. J. Med. Chem. 1995, 38, 3193-3196.
6. (b) Brömme, D.; Klaus, J. L.; Okamoto, K.; Rasnick, D.; Palmer, J. T. Biochem. J. 1996, 315, 85-89.
7. Olson, J. E.; Lee, G. K.; Semenov, A.; Rosenthal, P. J. Bioorg. Med. Chem. 1999, 7, 633-638.
8. See also: (a) Scheidt, K. A.; Roush, W. R.; McKerrow, J. H.; Selzer, P. M.; Hansell, E.; Rosenthal. P. J. Bioorg. Med. Chem. 1998, 6, 2477-2494.
9. (b) Kong, J.; Venkatraman, S.; Furness, K.; Nimkar, S.; Shepherd, T. A.; Wang, Q. M.; Aubé, J.; Hanzlik, R. P. J. Med. Chem. 1998, 41, 2579-2587.
10. (a) Bogyo, M.; McMaster, J. S.; Gaczynska, M.; Tortorella, D.; Goldberg, A. L.; Ploegh, H. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 6629-6634.
11. (b) Lee, D. H.; Goldberg, A. L. Trends Cell Biol. 1998, 397-403.
12. (c) Overkleeft, H. S.; Bos, P. R.; Hekking, B. G.; Gordon, E. J.; Ploegh, H. L.; Kessler, B. M. Tetrahedron Lett. 1999, 41, 6005-6009.
13. Sengupta, S.; Sarma, D. S.; Mondal, S. Tetrahedron: Asymmetry 1998, 9, 2311-2316.
14. For a recent example of the configurational lability of α-aminated aldehydes, see: List, B. J. Am. Chem. Soc. 2002, 124, 5656-5657.
15. (a) Catasús, M.; Bueno, A.; Moyano, A.; Maestro, M. A.; Mahía, J. J. Organomet. Chem. 2002, 642, 212-226.
16. (b) Martín, R.; Islas, G.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 2001, 57, 6367-6374.
17. (c) Medina, E., Moyano, A.; Pericàs, M. A.; Riera, A. Helv. Chim. Acta 2000, 83, 972-988.
18. (d) Catasús, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1999, 40, 9309-9312.
19. (e) Aguilar, N.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1999, 40, 3913-3916.
20. (f) Alcón, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1999, 10, 4639-4651.
21. (g) Aguilar, N.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 3560-3567 and references therein.
22. (a) Caron, M.; Carlier, P. R.; Sharpless, K. B. J. Org. Chem. 1988, 53, 5185-5187.
23. (b) Canas, M.; Poch, M.; Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 6931-6934.
24. (a) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922-1925.
25. (b) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
26. (c) Katsuki, T.; Martín, V. S. Org. React. 1996, 48, 1-299.
27. For the serendipitous formation of racemic γ-aryl-γ-amino vinyl sulfones, see: Woodgate, P. D.; Sutherland, H. S. J. Organomet. Chem. 2001, 628, 155-168.
28. Castejón, P.; Pastó, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1995, 36, 3019-3022.
29. For a related transformation, see: Luly, J. R.; Dellaria, J. F.; Platter, J. J.; Soderquist, J. L.; Yi, N. J. Org. Chem. 1987, 52, 1487-1492.
30. See: Bartoli, G.; Bellucci, M. C.; Petrini, M.; Marcantoni, E.; Sambri, L.; Torregiani, E. Org. Lett. 2000, 2, 1791-1793, and references therein.
31. (a) Aggarwal, V. K.; Lightowler, M.; Lindell, S. D. Synlett 1992, 730-732.
32. (b) Delouvrié, B.; Nájera F.; Fensterbank, L.; Malacria, M. J. Organomet. Chem. 2002, 643-644, 130-135.
33. 3CN, reflux, 11 h) afforded the corresponding vinyl sulfone 6cc in 92% yield.
34. Both the melting point and the rotatory power of the known vinyl sulfone 6bb were higher than those reported in the literature. Moreover, HPLC analysis established a 95% ee for this compound (see Experimental Section).
35. Thompson, S. A.; Andrews, P. R.; Hanzlik, R. P. J. Med. Chem. 1986, 29, 104-111.
36. See, inter alia: (a) Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903-917.
37. (b) Isobe, M. In Perspectives in the Organic Chemistry of Sulphur; Zwanenburg, D., Klunder, A. J. H., Eds.; Elsevier: New York, 1987; Vol. 28, pp 209-229.
38. (c) Nájera, C.; Yus, M. J. Org. Chem. 1989, 54, 1491-1499.
39. (d) Trost, B. M.; Seoane, P.; Mignani, P.; Acemoglu, J. J. Am. Chem. Soc. 1989, 111, 7487-7500.
40. (e) Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611-614.
41. (f) Domínguez, E.; Carretero, J. L. Tetrahedron 1990, 46, 7197-7206.
42. (g) Carretero, J. C.; Domínguez, E. J. Org. Chem. 1993, 58, 1596-1600.
43. (h) Enders, D.; Jandeleit, B.; von Berg, S. Synlett 1997, 421-431.
44. (i) de Vicente, J.; Gómez Arrayás, J.; Cañada, J. C.; Carretero, J. C. Synlett 2000, 53-56.
45. (j) Adrio, J.; Rodriguez Rivero, M.; Carretero, J. C. Chem. Eur. J. 2001, 7, 2435-2448.
46. (a) Pastó, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1996, 7, 243-262.
47. (b) Alcón, M.; Poch, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1997, 8, 2967-2974.
48. Barrish, J. C.; Gordon, E.; Alam, M.; Liu, P.-F.; Disacchi, G. S.; Chen, P.; Cheng, P. T. W.; Fritz, A. W.; Greytok, J. A.; Hermsmeier, M. A.; Humphreys, W. G.; Lis, K. A.; Marella, M. A.; Merchant, Z.; Mitt, T.; Morrison, R. A.; Obermeier, M. T.; Pluscec, J.; Skoog, M.; Slusarchyk, W. A.; Spergel, S. H.; Stevenson, J. M.; Sun, C.; Sundeen, J. E.; Taunk, P.; Tino, J. A.; Warrack, B. M.; Colonno, R. J.; Zahler, R. J. Med. Chem. 1994, 37, 1758-1768.
49. Romeo, S.; Rich, D. H. Tetrahedron Lett. 1993, 34, 7187-7190.