Asymmetric hydrogenation of N-sulfonylated-α-dehydroamino acids: Toward the synthesis of an anthrax lethal factor inhibitor

Organic Letters

Volumn 7, Issue 16, 2005, Pages 3405-3408

  Shultz, C Scott ^a   Dreher, Spencer D ^a   Ikemoto, Norihiro ^a   Williams, J Michael ^a   Grabowski, Edward J J ^a   Krska, Shane W ^a   Sun, Yongkui ^a   Dormer, Peter G ^a   DiMichele, Lisa ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANTHRAX TOXIN; BACTERIAL ANTIGEN; BACTERIAL TOXIN; RUTHENIUM;

ARTICLE; BACILLUS ANTHRACIS; CATALYSIS; CHEMISTRY; DRUG ANTAGONISM; HYDROGENATION; PATHOGENICITY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; ANTIGENS, BACTERIAL; BACILLUS ANTHRACIS; BACTERIAL TOXINS; CATALYSIS; HYDROGENATION; RUTHENIUM; STEREOISOMERISM;

EID: 23944494085     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050869s     Document Type: Article

References (37)

1. Shoop, W. L.; Xiong, Y.; Wiltsie, J.; Woods, A.; Guo, J.; Pivnichny, J. V.; Felcetto, T.; Michael, B. F.; Bansal, A.; Cummings, R. T.; Cunningham, B. R.; Friedlander, A. M.; Douglas, C. M.; Patel, S. B.; Wisniewski, D.; Scapin, G.; Salowe, S. P.; Zaller, D. M.; Chapman, K. T.; Scolnick, E. M.; Schmatz, D. M.; Bartizal, K.; MacCoss, M.; Hermes, J. D. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 7958-7963.
2. Full details of these experiments are reported in an upcoming publication.
3. Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375-9376.
4. For example, see: (a) Kottirsch, G.; Zerwes, H.-G.; Cook, N. S.; Tapparelli, C. Bioorg. Med. Chem. Lett. 1997, 7, 727.
5. (b) O'Brien, P. M.; Ortwine, D. F.; Pavlovsky, A. G.; Picard, J. A.; Sliskovic, D. R.; Roth, B. D.; Dyer, R. D.; Johnson, L. L.; Man, C. F.; Hallak, H. J. Med. Chem. 2000, 43, 156.
6. (c) Pikul, S.; Ohler, N. E.; Ciszewski, G.; Laufersweiler, M. C.; Almstead, N. G.; De, B.; Natchus, M. G.; L. C., H.; Janusz, M. J.; Peng, S. X.; Branch, T. M.; King, S. L.; Taiwo, Y. O.; G. E., M. J. Med. Chem. 2001, 44, 2499.
7. (d) Dankwardt, S. M.; Abbot, S. C.; Broka, C. A.; Martin, R. L.; Chan, C. S.; Springman, E. B.; Van Wart, H. E.; Walker, K. A. M. Bioorg. Med. Chem. Lett. 2002, 12, 1233.
8. Recently, Ito has reported the asymmetric hydrogenation of an N-sulfonylated indole with a Rh catalyst. Kuwano, R.; Kaneda, K.; Ito, T.; Sato, K.; Kurokawa, T.; Ito, Y. Org. Lett. 2004, 6, 2213-2215.
9. For example, see: (a) Sawamura, M.; Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9602.
10. (b) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207.
11. (c) Kuwano, R.; Okuda, S.; Ito, Y. J. Org. Chem. 1998, 63, 3499.
12. (d) Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988-2989
13. (e) Blaser, H.-U.; Spindler, F.; Studer, M. Appl. Catal., A 2001, 221, 119-143.
14. (f) Sheih, W.-C.; Xue, S.; Reel, N.; Wu, R.; Fitt, J.; Repic, O. Tetrahedron: Asymmetry 2001, 12, 2421.
15. (g) Liu, D.; Li, W.; Zhang, X. Org. Lett. 2002, 4, 4471
16. (h) Ohashi, A.; Kikuchi, S.-i.; Yasutake, M.; Imamoto, T. Eur. J. Org. Chem. 2002, 2535.
17. Lennon, I. C.; Moran, P. H. Curr. Opin. Drug Discovery Dev. 2003, 6, 855-875.
18. (j) Blaser, H. U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103.
19. (k) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
20. Asymmetric hydrogenation of tetrasubstituted amide-protected α-amino acids with Rh catalysts is known: (a) Takahashi, H.; Achiwa, K. Chem. Lett. 1989, 2, 305.
21. (b) Nagel, U.; Kinzel, E. Chem. Ber. 1986, 119, 3326.
22. Ikariya, T.; Ishii, Y.; Kawano, H.; Arai, T.; Saburi, M.; Yoshikawa, S.; Akutagawa, S. J. Chem. Soc., Chem. Commun. 1985, 922.
23. Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans, 1 1989, 1571.
24. A Ru catalyst has been used to hydrogenate a tetrasubstituted enamide; see: Dupau, P.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2001, 343, 331-334.
25. 2 + phosphine ligand in 3:1 EtOH/1,2-dichloroethane at 50°C for ≥1 h. See Supporting Information for complete details.
26. Yonezawa, Y.; Shin, C.; Ono, Y.; Yoshimura, J. Bull. Chem. Soc. Jpn. 1980, 53, 2905.
27. A small amount of high-boiling diethylene glycol diethyl ether was employed to keep the polar materials in solution during the reaction.
28. 2 pressure and had no effect on reaction ee.
29. Benincori, T.; Cesarotti, E.; Piccolo, O.; Sannicolò, F. J. Org. Chem. 2000, 65, 2043-2047.
30. 2.
31. Liu, D.; Li, W.; Zhang, X. Org. Lett. 2002, 4, 4471-4474.
32. 2, 25°C, 24 h), and the highest ee observed was approximately 30% with the TMBTP ligand.
33. Compounds 5a (52% isolated yield) and 5b (43%) were prepared similar to: Yonezawa, Y.; Shin, C.; Ono, Y.; Yoshimura, J. Bull. Chem. Soc. Jpn. 1980, 53, 2905.
34. Dehydro-isoleucine substrates (E)-7 and (Z)-7 were prepared as a 1.25:1 (E/Z) mixture in 70% yield and separated via preparative SFC. See Supporting Information for details. Olefin geometry for (E)-7 was determined on the basis of observed NOE (0.3%) at the o-phenyl of the Ts sulfonamide upon selective excitation of the methyl singlet.
35. Diastereomer ratio reported is the ratio of the HPLC absorbance of each diastereomer at 224 nm.
36. Ashby, M. T.; Halpern, J. J. Am. Chem. Soc. 1991, 113, 589-594.
37. 2 gas being much faster than the rate of hydrogenation.