Two complementary, diversity-driven asymmetric syntheses of a 2,2-disubstituted piperidine NK1 antagonist

Tetrahedron Asymmetry

Volumn 17, Issue 18, 2006, Pages 2596-2598

  Xiao, Dong ^a   Wang, Cheng ^a   Palani, Anandan ^a   Reichard, Gregory ^a   Aslanian, Robert ^a   Shih, Neng Yang ^a   Buevich, Alexei ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NEUROKININ 1 RECEPTOR ANTAGONIST; PIPERIDINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 33750514347     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.09.022     Document Type: Article

References (30)

1. Xiao D., Lavey B., Wang C., Palani A., Aslanian R., Kozlowski J., Shih N.-Y., McPhail A.T., Randolph G.P., Lachowicz J.E., and Duffy R.A. Tetrahedron Lett. 46 (2005) 7653
2. Harrison T., Willaims B.J., and Swain C.J. Bioorg. Med. Chem. Lett. (1994) 2733
3. Xiujian W., Dubois K., Rogiers J., Toppet S., Compernolle F., and Hoornaert G.J. Tetrahedron 56 (2000) 3043
4. Rogiers J., De Borggraeve W.M., Toppet S.M., Compernolle F., and Hoornaert G.J. Tetrahedron 59 (2003) 5047
5. For recent reviews:. Bailey P.D., Millwood P.A., and Smith P.D. J. Chem. Soc., Chem. Commun. (1998) 633
6. Laschat S., and Dickner T. Synthesis 13 (2000) 1781
7. Weintraub P.M., Sabol J.S., Kane J.M., and Borcherding D.R. Tetrahedron 59 (2003) 2953
8. Buffat M.P.G. Tetrahedron 60 (2004) 1701
9. For recent examples:. Kawabata T., Kawakami S., and Majumdar S. J. Am. Chem. Soc. 125 (2003) 13012
10. Kawabata T., Majumdar S., Tsubaki K., and Monguchi D. Org. Biomol. Chem. 3 (2005) 1609
11. Hou D.-R., Hung S.-Y., and Hu C.-C. Tetrahedron: Asymmetry 16 (2005) 3858 and references cited therein
12. For leading reviews:. Davis F.A., Zhou P., and Chen B.-C. Chem. Soc. Rev. 27 (1998) 13
13. Ellman J.A., Owens T.D., and Tang T.P. Acc. Chem. Res. 35 (2002) 984
14. Ellman J.A. Pure Appl. Chem. 75 (2003) 39
15. Zhou P., Chen B.-C., and Davis F.A. Tetrahedron 60 (2004) 8003
16. For recent examples of application of chiral sulfinimines in piperidine synthesis:. Davis F.A., Zhang J., Li Y., Xu H., and DeBrosse C. J. Org. Chem. 70 (2005) 5413
17. Peltier H.M., and Ellman J.A. J. Org. Chem. 70 (2005) 7342 and references cited therein
18. Reichard G.A., Stengone C., Paliwal S., Mergelsberg I., Majmundar S., Wang C., Tiberi R., McPhail A., Piwinski J.J., and Shih N.-Y. Org. Lett. 5 (2003) 4249
19. Liu G., Cogan D.A., and Ellman J.A. J. Am. Chem. Soc. 119 (1997) 9913
20. Cogan D.A., Liu G., and Ellman J.A. J. Am. Chem. Soc. 120 (1998) 8011
21. Liu G., Cogan D.A., Owens T.D., Tang T.P., and Ellman J.A. J. Org. Chem. 64 (1999) 1278
22. Cogan D.A., Liu G., and Ellman J.A. Tetrahedron 55 (1999) 8883
23. For recent reviews:. Pandit U.K., Overkleekt H.S., Borer B.C., and Bieraugel H. Eur. J. Org. Chem. (1999) 959
24. Felpin F.-X., and Lebreton J. Eur. J. Org. Chem. (2003) 3693
25. Choi T.-L., Chatterjee A.K., and Grubbs R.H. Angew. Chem., Int. Ed. 40 (2001) 1277
26. Husson H.-P., and Royer J. Chem. Soc. Rev. 28 (1999) 383
27. For recent examples:. Malassene R., Vanquelef E., Toupet L., Hurvois J.-P., and Moinet C. Org. Biomol. Chem. 1 (2003) 547
28. Pave G., Leger J.-M., Jarry C., Viaud-Massuard M.-C., and Guillaumet G. J. Org. Chem. 68 (2003) 1401
29. The stereochemistry of 12 was assigned by HMBC and NOE studies. The detailed information of NMR studies and characterization of all new compounds will be published in a full account in the near future.
30. Yue C., Royer J., and Husson H.P. J. Org. Chem. 57 (1992) 4211