Design of new polyamine-based chiral phase-transfer catalysts for the enantioselective synthesis of phenylalanine

Tetrahedron Asymmetry

Volumn 15, Issue 8, 2004, Pages 1243-1245

  Kano, Taichi ^a   Konishi, Shunsuke ^a   Shirakawa, Seiji ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCINE; PHENYLALANINE DERIVATIVE; POLYAMINE; SCHIFF BASE;

ARTICLE; BENZYLATION; CATALYST; CHIRALITY; DRUG DESIGN; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; PHASE TRANSITION; PRIORITY JOURNAL;

EID: 1842737439     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.02.023     Document Type: Article

References (33)

1. For reviews, see: Ojima I. Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley-VCH, New York.
2. Jacobsen E.N., Phaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. 1999;Springer, Heidelberg.
3. Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;Wiley, New York.
4. Dalko P.I., Moison L. Angew. Chem., Int. Ed. 40:2001;3727.
5. For reviews, see: Shioiri T. Sasson Y., Neumann R. Handbook of Phase Transfer Catalysis. 1997;Blackie Academic & Professional, London. Chapter 14.
6. Ebrahim S., Wills M. Tetrahedron: Asymmetry. 8:1997;3163.
7. Esikova I.A., Nahreini T.S., O'Donnell M.J. Phase-Transfer Catalysis. ACS Symp. Ser. 659. 1997;American Chemical Society, Washington, DC. Chapter 7.
8. Shioiri T., Ando A., Masui M., Miura T., Tatematsu T., Bohsako A., Higashiyama M., Asakura C. Phase-Transfer Catalysis. ACS Symp. Ser. 629. 1997;American Chemical Society, Washington, DC. Chapter 11.
9. O'Donnell M.J. Catalytic asymmetric synthesis. Ojima I. Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley-VCH, New York. Chapter 10.
10. O'Donnell M.J. Aldrichim. Acta. 34:2001;3.
11. Maruoka K., Ooi T. Chem. Rev. 103:2003;3013.
12. For representative examples: O'Donnell M.J., Wu S., Huffman J.C. Tetrahedron. 50:1994;4507.
13. Corey E.J., Xu F., Noe M.C. J. Am. Chem. Soc. 119:1997;12414.
14. Arai S., Shirai Y., Ishida T., Shioiri T. Chem. Commun. 1999;49.
15. Lygo B., Crosby J., Peterson J.A. Tetrahedron Lett. 40:1999;8671.
16. Zhang F.-Y., Corey E.J. Org. Lett. 2:2000;1097.
17. Belokon Y.N., Davies R.G., North M. Tetrahedron Lett. 41:2000;7245.
18. Ooi T., Kameda M., Maruoka K. J. Am. Chem. Soc. 121:1999;6519.
19. Ooi T., Takeuchi M., Kameda M., Maruoka K. J. Am. Chem. Soc. 122:2000;5228.
20. Ooi T., Takeuchi M., Ohara D., Maruoka K. Synlett. 2001;1185.
21. Ooi T., Takeuchi M., Maruoka K. Synthesis. 2001;1716.
22. Ooi T., Uematsu Y., Kameda M., Maruoka K. Angew. Chem., Int. Ed. 41:2002;1551.
23. Maruoka K. J. Fluorine Chem. 112:2001;95.
24. Ooi T., Uematsu Y., Maruoka K. Adv. Synth. Catal. 344:2002;288.
25. Ooi T., Taniguchi M., Kameda M., Maruoka K. Angew. Chem., Int. Ed. 41:2002;4542.
26. Ooi T., Tayama E., Maruoka K. Angew. Chem., Int. Ed. 42:2003;579.
27. Ooi T., Kameda M., Maruoka K. J. Am. Chem. Soc. 125:2003;5139.
28. Hashimoto T., Maruoka K. Tetrahedron Lett. 44:2003;3313.
29. Hashimoto T., Tanaka Y., Maruoka K. Tetrahedron: Asymmetry. 14:2003;1599.
30. 4 requires 658.3348).
31. Recently bis- or tris-ammonium salts as phase-transfer catalysts have been reported: Park H., Jeong B., Yoo M., Park M., Huh H., Jew S. Tetrahedron Lett. 42:2001;4645.
32. Jew S., Jeong B., Yoo M., Huh H., Park H. Chem. Commun. 2001;1244.
33. Shibuguchi T., Fukuta Y., Akachi Y., Sekine A., Ohshima T., Shibasaki M. Tetrahedron Lett. 43:2002;9539.