Combinatorial approach for the design of new, simplified chiral phase-transfer catalysts with high catalytic performance for practical asymmetric synthesis of α-alkyl-α-amino acids

Tetrahedron Letters

Volumn 49, Issue 12, 2008, Pages 2026-2030

  Kitamura, Masanori ^a   Arimura, Yuichiro ^a   Shirakawa, Seiji ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHIRAL CHROMATOGRAPHY; COMBINATORIAL CHEMISTRY; ENANTIOSELECTIVITY; PROTEIN STRUCTURE; PROTEIN SYNTHESIS;

EID: 39249084667     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.029     Document Type: Article

References (56)

1. Recent representative reviews on asymmetric PTC:. Shioiri T. In: Sasson Y., and Neumann R. (Eds). Handbook of Phase-Transfer Catalysis (1997), Blackie Academic & Professional, London Chapter 14
2. O'Donnell M.J. In: Ojima I. (Ed). Catalytic Asymmetric Syntheses. 2nd ed. (2000), WILEY-VCH, New York Chapter 10
3. Shioiri T., and Arai S. In: Vogtle F., Stoddart J.F., and Shibasaki M. (Eds). Stimulating Concepts in Chemistry (2000), WILEY-VCH, Weinheim 123
4. O'Donnell M.J. Aldrichim. Acta 34 (2001) 3
5. Maruoka K., and Ooi T. Chem. Rev. 103 (2003) 3013
6. O'Donnell M.J. Acc. Chem. Res. 37 (2004) 506
7. Lygo B., and Andrews B.I. Acc. Chem. Res. 37 (2004) 518
8. Maruoka K., Ooi T., and Kano T. Chem. Commun. (2007) 1487
9. Ooi T., and Maruoka K. Angew. Chem., Int. Ed. 46 (2007) 4222
10. Ooi T., and Maruoka K. Aldrichim. Acta 40 (2007) 77
11. Hashimoto T., and Maruoka K. Chem. Rev. 107 (2007) 5656
12. Ooi T., Kameda M., and Maruoka K. J. Am. Chem. Soc. 125 (2003) 5139
13. O'Donnell M.J., Bennett W.D., and Wu S. J. Am. Chem. Soc. 111 (1989) 2353
14. Corey E.J., Xu F., and Noe M.C. J. Am. Chem. Soc. 119 (1997) 12414
15. Lygo B., and Wainwright P.G. Tetrahedron Lett. 38 (1997) 8595
16. O'Donnell M.J., Delgado F., Hostettler C., and Schweinger R. Tetrahedron Lett. 39 (1998) 8775
17. Jew S.-s., Jeong B.-S., Yoo M.-S., Huh H., and Park H.-g. Chem. Commun. (2001) 1244
18. Park H.-g., Jeong B.-S., Yoo M.-S., Park M.-k., Huh H., and Jew S.-s. Tetrahedron Lett. 42 (2001) 4645
19. Nakoji M., Kanayama T., Okino T., and Takemoto Y. Org. Lett. 3 (2001) 3329
20. Park H.-g., Jeong B.-S., Yoo M.-S., Lee J.-H., Park M.-k., Lee Y.-J., Kim M.-J., and Jew S.-s. Angew. Chem., Int. Ed. 41 (2002) 3036
21. Kita T., Georgieva A., Hashimoto U., Nakata T., and Nagasawa K. Angew. Chem., Int. Ed. 41 (2002) 2832
22. Shibuguchi T., Fukuta Y., Akachi Y., Sekine A., Ohshima T., and Shibasaki M. Tetrahedron Lett. 43 (2002) 9539
23. Lygo B., Allbutt B., and James S.R. Tetrahedron Lett. 44 (2003) 5629
24. Belokon Y.N., Bespalova N.B., Churkina T.D., Císarová I., Ezernitskaya M.G., Harutyunyan S.R., Hrdina R., Kagan H.B., Kocovsky P., Kochetkov K.A., Larionov O.V., Lyssenko K.A., North M., Polásek M., Peregudov A.S., Prisyazhnyuk V.V., and Vyskocil S. J. Am. Chem. Soc. 125 (2003) 12860
25. Park H.-g., Jeong B.-S., Yoo M.-S., Lee J.-H., Park B.-s., Kim M.G., and Jew S.-s. Tetrahedron Lett. 44 (2003) 3497
26. Mase N., Ohno T., Hoshikawa N., Ohishi K., Morimoto H., Yoda H., and Takabe K. Tetrahedron Lett. 44 (2003) 4073
27. Chinchilla R., Mazon P., and Najera C. Tetrahedron: Asymmetry 13 (2002) 927
28. Kowtoniuk W.E., Rueffer M.E., and MacFarland D.K. Tetrahedron: Asymmetry 15 (2004) 151
29. Rueffer M.E., Fort L.K., and MacFarland D.K. Tetrahedron: Asymmetry 15 (2004) 3297
30. Yoo M.-S., Jeong B.-S., Lee J.-H., Park H.-g., and Jew S.-s. Org. Lett. 7 (2005) 1129
31. Siva A., and Murugan E. J. Mol. Catal. A: Chem. 248 (2006) 1
32. Yonezawa, H.; Shimomoto, A.; Takizawa, S.; Sasai, H. Jpn. Kokai Tokkyo Koho 2006, JP 2006070001.
33. Chinchilla R., Nájera C., and Ortega F.J. Tetrahedron: Asymmetry 17 (2006) 3423
34. Lee J.-H., Jeong B.-S., Ku J.-M., Jew S.-s., and Park H.-g. J. Org. Chem. 71 (2006) 6690
35. Wang X., Yin L., Yang T., and Wang Y. Tetrahedron: Asymmetry 18 (2007) 108
36. Ooi T., Kameda M., and Maruoka K. J. Am. Chem. Soc. 121 (1999) 6519
37. Ooi T., Kameda M., Tannai H., and Maruoka K. Tetrahedron Lett. 41 (2000) 8339
38. Maruoka K. J. Fluorine Chem. 112 (2001) 95
39. Ooi T., Uematsu Y., Kameda M., and Maruoka K. Angew. Chem., Int. Ed. 41 (2002) 1551
40. Ooi T., Takahashi M., Doda K., and Maruoka K. J. Am. Chem. Soc. 124 (2002) 7640
41. Ooi T., Kubota Y., and Maruoka K. Synlett (2003) 1931
42. Ooi T., Sakai D., Takeuchi M., Tayama E., and Maruoka K. Angew. Chem., Int. Ed. 42 (2003) 5868
43. Hashimoto T., and Maruoka K. Tetrahedron Lett. 44 (2003) 3313
44. Hashimoto T., Tanaka Y., and Maruoka K. Tetrahedron: Asymmetry 14 (2003) 1599
45. Ooi T., Uematsu Y., and Maruoka K. Tetrahedron Lett. 45 (2004) 1675
46. Shirakawa S., Tanaka Y., and Maruoka K. Org. Lett. 6 (2004) 1429
47. Shirakawa S., Yamamoto K., Kitamura M., Ooi T., and Maruoka K. Angew. Chem., Int. Ed. 44 (2005) 625
48. Ooi T., Takeuchi M., Kato D., Uematsu Y., Tayama E., Sakai D., and Maruoka K. J. Am. Chem. Soc. 127 (2005) 5073
49. Ooi T., Arimura Y., Hiraiwa Y., Yuan L.M., Kano T., Inoue T., Matsumoto J., and Maruoka K. Tetrahedron: Asymmetry 17 (2006) 603
50. Han Z., Yamaguchi Y., Kitamura M., and Maruoka K. Tetrahedron Lett. 46 (2005) 8555
51. Kano T., Lan Q., Wang X., and Maruoka K. Adv. Synth. Catal. 349 (2007) 556
52. Wang Y.-G., and Maruoka K. Org. Process Res. Dev. 11 (2007) 628
53. Wang Y.-G., Ueda M., Wang X., Han Z., and Maruoka K. Tetrahedron 63 (2007) 6042
54. Kitamura M., Shirakawa S., and Maruoka K.. Angew. Chem., Int. Ed. 44 (2005) 1549
55. Seki M., Yamada S., Kuroda T., Imashiro R., and Shimizu T. Synthesis (2000) 1677
56. Ooi T., Uematsu Y., and Maruoka K. J. Org. Chem. 68 (2003) 4576