A new polymer-supported Evans-type chiral auxiliary derived from α-hydroxy-β-amino acid, phenylnorstatine: Synthesis and application in solid-phase asymmetric alkylation reactions

Tetrahedron Letters

Volumn 45, Issue 18, 2004, Pages 3651-3654

  Kotake, Tomoya ^a   Rajesh, S ^a   Hayashi, Yoshio ^a   Mukai, Yoshie ^a   Ueda, Mitsuhiro ^a   Kimura, Tooru ^a   Kiso, Yoshiaki ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Asymmetric alkylation; Chiral auxiliary; Evans' oxazolidinone; Phenylnorstatine; Polymer supported; Solid phase

Indexed keywords

3 AMINO 2 HYDROXY 4 PHENYLBUTYRIC ACID; ALPHA HYDROXY BETA AMINO ACID; AMINO ACID DERIVATIVE; OXAZOLIDINONE DERIVATIVE; POLYMER; RESIN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHIRALITY; COMPARATIVE STUDY; EXPERIMENT; MODEL; REACTION ANALYSIS; SOLID; STEREOCHEMISTRY; SYNTHESIS;

EID: 1842686330     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.043     Document Type: Article

References (29)

1. Seneci P. Solid Phase and Combinatorial Technologies. 2000;John Wiley & Sons, New York.
2. Obrecht D., Villalgordo J.M. Solid-Supported Combinatorial and Parallel Synthesis of Small Molecular-Weight Compound Libraries. Tetrahedron Organic Chemistry Series. Vol. 17:1998;Elsevier, Oxford.
3. Geysen H.M., Schoenen F., Wagner D., Wagner R. Nat. Rev. Drug Discovery. 2:2003;222-230.
4. Gallop M.A., Barrett R.W., Dower W.J., Fodor S.P.A., Gordon E.M. J. Med. Chem. 37:1994;1233-1251.
5. Evans D.A. Aldrichim. Acta. 15:1982;23-32.
6. Ager D.J., Prakash I., Schaad D.R. Aldrichim. Acta. 30:1997;3-11.
7. Burgess K., Lim D. Chem. Commun. 1997;785-786.
8. Purandare A.V., Natarajan S. Tetrahedron Lett. 38:1997;8777-8780.
9. Phoon C.W., Abell C. Tetrahedron Lett. 39:1998;2655-2658.
10. Winkler J.D., McCoull W. Tetrahedron Lett. 39:1998;4935-4936.
11. Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269.
12. Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron. 57:2001;8313-8322.
13. Desimoni G., Faita G., Galbiati A., Pasini D., Quadrelli P., Rancati F. Tetrahedron: Asymmetry. 13:2002;333-337.
14. Mimoto T., Kato R., Takaku H., Nojima S., Terashima K., Misawa S., Fukazawa T., Ueno T., Sato H., Shintani M., Kiso Y., Hayashi H. J. Med. Chem. 42:1999;1789-1802.
15. Mimoto T., Hattori N., Takaku H., Kisanuki S., Fukazawa T., Terashima K., Kato R., Nojima S., Misawa S., Ueno T., Imai J., Enomoto H., Tanaka S., Sakikawa H., Shintani M., Hayashi H., Kiso Y. Chem. Pharm. Bull. 48:2000;1310-1326.
16. Wang resin was purchased from Watanabe Chem. Ind., Ltd (Hiroshima, Japan), loading 0.75 mmol/g, 100-200 mesh, polystyrene with 1% cross linking with divinylbenzene.
17. Boc-Pns-OH was prepared from H-Pns-OH, which was purchased from Nippon Kayaku (Tokyo, Japan).
18. König W., Geiger R. Chem. Ber. 103:1970;788-798.
19. Bunnage M.E., Davies S.G., Goodwin C.J., Ichihara O. Tetrahedron. 50:1994;3975-3986.
20. 5: C, 68.23; H, 6.20; N, 6.63. Found: C, 67.99; H, 6.20; N, 6.55.
21. Cutugno S., Martelli G., Negro L., Savoia D. Eur. J. Org. Chem. 2001;517-522.
22. 16 and then the product was purified by preparative TLC for removing nonalkylated carboxylic acid. The resultant pure 7 was next coupled with (S)-phenylethylamine by the EDC-HOBt method to determine the enantiomeric excesses of the α-alkylated carboxylic acids 7 by HPLC.
23. Evans D.A., Britton T.C., Ellman J.A. Tetrahedron Lett. 28:1987;6141-6144.
24. Evans D.A., Ellman J.A. J. Am. Chem. Soc. 111:1989;1063-1072.
25. Atherton E., Benoiton N.L., Brown E., Sheppard R.C., Williams B.J. J. Chem. Soc., Chem. Commun. 1981;336-337.
26. Ho G.-J., Mathre D.J. J. Org. Chem. 60:1995;2271-2273.
27. Mukaiyama T. Angew. Chem., Int. Ed. Engl. 18:1979;707-721.
28. The crude product 7 was purified by preparative TLC to remove nonalkylated carboxylic acid. The relatively lower yield (38-54%) that was observed in the solid-phase method was due to the fact that the yield includes the four step reaction from Wang resin to the final product 7. The yield for two steps (alkylation and hydrolysis) is likely to be similar to that of the solution-phase method.
29. Kim D.H., Li Z.-H., Lee S.S., Park J., Chung S.J. Bioorg. Med. Chem. 6:1998;239-249.