Dynamic kinetic resolution (DKR) using immobilized amine nucleophiles

Tetrahedron Letters

Volumn 45, Issue 12, 2004, Pages 2545-2549

  Valenrod, Yevgeny ^a   Myung, Jinnie ^a   Ben, Robert N ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

Dynamic kinetic resolution; Immobilized amine; Resin bound amine; Solid phase

Indexed keywords

ALPHA AMINO ACID; AMINE; ESTER DERIVATIVE; RESIN;

ALKYLATION; ARTICLE; DIASTEREOISOMER; DYNAMICS; KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 1542362260     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.004     Document Type: Article

References (29)

1. Houghten R.A., Pinilla C., Blondelle S.E., Appel J.R., Dooley C.T., Cuervo J.H. Nature. 354:2001;84.
2. Jung G., Beck-Sickinger A.G. Angew. Chem., Int. Ed. Engl. 31:1992;367.
3. Zheng C., Seeberger P.H., Danishefsky S.J. J. Org. Chem. 63:1998;1126.
4. Ecker D.J., Vickers T.A., Hanecak R., Driver V., Anderson K. Nucleic Acids Res. 21:1993;1853.
5. Armstrong R.W., Combs A.P., Tempest P.A., Brown S.D., Keating T.A. Acc. Chem. Res. 29:1996;123.
6. Wilson S.R., Czarnik A.W. Combinatorial Chemistry, Synthesis and Application. 1997;New York, Wiley.
7. An H., Cook P.D. Chem. Rev. 100:2000;3311.
8. For solid supported dienophiles see: Winkler J.D., Kwak Y.-S. J. Org. Chem. 63:1998;8634.
9. Sun S., Murray W.V. J. Org. Chem. 64:1999;5941.
10. Kuster G.J., Scheeren H.W. Tetrahedron Lett. 41:2000;515.
11. Zhang W., Xie W., Fang J., Wang P.G. Tetrahedron Lett. 40:1999;7929.
12. Burkett B.A., Chai C.L.L. Tetrahedron Lett. 40:1999;7035.
13. For solid supported dipolarophiles see: Tan D.S., Foley M.A., Stockwell B.R., Shari M.D., Schreiber S.L. J. Am. Chem. Soc. 121:1999;9073.
14. Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967.
15. Zhao C., Shi S., Mir D., Hurst D., Li R., Xiao X., Lillig J., Czarnik A.W. J. Comb. Chem. 1:1999;91.
16. Park K.-H., Kurth M. J. Chem. Commun. 2000;1835.
17. Winkler J.D., McCoull W. Tetrahedron Lett. 39:1998;4935.
18. Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron. 57:2001;8313.
19. Lysek R., Furman B., Cierpucha M., Grzeszczyk B., Matyjasek L., Chmielewski M. Eur. J. Chem. 2002;2377.
20. Tremblay M.R., Wentworth P. Jr., Lee G.E., Janda K.D. J. Comb. Chem. 2:2000;698.
21. For a general review on kinetic resolutions see: Kagan H.B., Fiaud J.C. Top. Stereochem. 18:1988;249.
22. For examples of dynamic kinetic resolutions see: Noyori R., Ikeda T., Ohkuma T., Widhalm M., Kitamura M., Takya H., Sayo N., Saito T., Taketomi T., Kumobayashi H. J. Am. Chem. Soc. 111:1989;9134.
23. Sheih W.-C., Carlson J.A., Zaunius G.M. J. Org. Chem. 62:1997;8271.
24. Kubota H., Kubo A., Takahashi M., Shimizu R., Date T., Okamura K., Nunami K. J. Org. Chem. 60:1995;6776.
25. Durst T., Koh K. Tetrahedron Lett. 33:1992;6799.
26. Ben R.N., Durst T. J. Org. Chem. 64:1999;7700.
27. O'Meara J., Gardee N., Jung M., Ben R.N., Durst T. J. Org. Chem. 63:1998;3117.
28. Koh K., Ben R.N., Durst T. Tetrahedron Lett. 35:1994;375.
29. Koh K., Ben R.N., Durst T. Tetrahedron Lett. 34:1993;4473.