Catalytic asymmetric synthesis of cyclic amino acids and alkaloid derivatives: Application to (+)-dihydropinidine and Selfotel synthesis

Chemical Science

Volumn 1, Issue 4, 2010, Pages 499-501

  Kano, Taichi ^a   Kumano, Takeshi ^a   Sakamoto, Ryu ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC ALKYLATION; ASYMMETRIC SYNTHESIS; CORE STRUCTURE; CYCLIC AMINO ACIDS; N-METHYL-D-ASPARTATE; REDUCTIVE AMINATION;

AMINATION; METABOLITES; NITROGEN COMPOUNDS;

AMINO ACIDS;

EID: 80052947452     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c0sc00250j     Document Type: Article

References (55)

1. P. I. Dalko and L. Moisan, Angew. Chem., Int. Ed., 2001, 40, 3726
2. P. I. Dalko and L. Moisan, Angew. Chem., Int. Ed., 2004, 43, 5138
3. A. Berkessel and H. Groger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005
4. Enantioselective Organocatalysis, ed. P. I. Dalko, Wiley-VCH, Weinheim, 2007
5. H. Pellissier, Tetrahedron, 2007, 63, 9267
6. T. Shioiri, in Handbook of Phase Transfer Catalysis, ed. Y. Sasson and R. Neumann, Blackie Academic & Professional, London, 1997, ch. 14
7. S. Ebrahim and M. Wills, Tetrahedron: Asymmetry, 1997, 8, 3163
8. I. A. Esikova, T. S. Nahreini, and M. J. ODonnell, in Phase-Transfer Catalysis, ed. H. E. Halpern, ACS Symposium Series 659, American Chemical Society, Washington, DC, 1997, ch. 7
9. T. Shioiri, A. Ando, M. Masui, T. Miura, T. Tatematsu, A. Bohsako, M. Higashiyama and C. Asakura, in Phase-Transfer Catalysis, ed. M. E. Halpern, ACS Symposium Series 659, American Chemical Society, Washington, DC, 1997, ch. 11
10. M. J. ODonnell, in Catalytic Asymmetric Synthesis, 2nd edn, ed. I. Ojima, Wiley-VCH, New York, 2000, ch. 10
11. M. J. ODonnell, Aldrichimica Acta, 2001, 34, 3
12. K. Maruoka and T. Ooi, Chem. Rev., 2003, 103, 3013
13. T. Ooi and K. Maruoka, Angew. Chem., Int. Ed., 2007, 46, 4222
14. Y.-G. Wang, T. Kumano, T. Kano and K. Maruoka, Org. Lett., 2009, 11, 2027
15. P. D. Bailey, P. A. Millwood and P. D. Smith, Chem. Commun., 1998, 633
16. F. Couty, Amino Acids, 1999, 16, 297
17. M. G. P. Buffat, Tetrahedron, 2004, 60, 1701
18. C. Kadouri-Puchot and S. Comesse, Amino Acids, 2005, 29, 101
19. K. Kitamura, S. Shirakawa and K. Maruoka, Angew. Chem., Int. Ed., 2005, 44, 1549
20. M. Kitamura, S. Shirakawa, Y. Arimura, X. Wang and K. Maruoka, Chem.-Asian J., 2008, 3, 1702
21. Under similar conditions, the reaction between 1 and the corresponding alkyl iodide gave 4a with slightly lower enantioselectivity (74%, 85% ee)
22. M. E. Swarbrick, F. Gosselin and W. D. Lubell, J. Org. Chem., 1999, 64, 1993
23. F. A. Davis, H. Zhang and S. H. Lee, Org. Lett., 2001, 3, 759
24. H. Takahata and M. Shimizu, Amino Acids, 2003, 24, 267 and references therein
25. R. K. Hill and T. Yuri, Tetrahedron, 1977, 33, 1569
26. L. Guerrier, J. Royer, D. S. Grierson and H.-P. Husson, J. Am. Chem. Soc., 1983, 105, 7754
27. E. Theodorakis, J. Royer and H.-P. Husson, Synth. Commun., 1991, 21, 521
28. H. Takahata, H. Bandoh, M. Hanayama and T. Momose, Tetrahedron: Asymmetry, 1992, 3, 607
29. Z.-H. Lu and W.-S. Zhou, J. Chem. Soc., Perkin Trans. 1, 1993, 593
30. E. Lee, T. S. Kang, B. J. Joo, J. S. Tae, K. S. Li and C. K. Chung, Tetrahedron Lett., 1995, 36, 417
31. R. Chenevert and M. Dickman, J. Org. Chem., 1996, 61, 3332
32. T. Momose, M. Toshima, N. Toyooka, Y. Hirai and C. H. Eugster, J. Chem. Soc., Perkin Trans. 1, 1997, 1307
33. O. Muraoka, B.-Z. Zheng, K. Okumura, E. Tabata, G. Tanabe and M. Kubo, J. Chem. Soc., Perkin Trans. 1, 1997, 113
34. A. R. Katritzky, G. Qiu, B. Yang and P. J. Steel, J. Org. Chem., 1998, 63, 6699
35. F. A. Davis and J. M. Szewczyk, Tetrahedron Lett., 1998, 39, 5951
36. T. Yamauchi, H. Fujikura, K. Higashiyama, H. Takahashi and S. Ohmiya, J. Chem. Soc., Perkin Trans. 1, 1999, 2791
37. T. J. Wilkinson, N. W. Stehle and P. Beak, Org. Lett., 2000, 2, 155
38. S. Ciblat, P. Besse, V. Papastergiou, H. Veschambre, J.-L. Canet and Y. Troin, Tetrahedron: Asymmetry, 2000, 11, 2221
39. S. Freville, P. Delbecq, V. M. Thuy, H. Petit, J. P. Celerier and G. Lhommet, Tetrahedron Lett., 2001, 42, 4609
40. M. Amat, N. Llor, J. Hidalgo, C. Escolano and J. Bosch, J. Org. Chem., 2003, 68, 1919
41. C. Shu and L. S. Liebeskind, J. Am. Chem. Soc., 2003, 125, 2878
42. B. Kranke, D. Hebrault, M. Schultz-Kukula and H. Kunz, Synlett, 2004, 671
43. L. F. Roa, D. Gnecco, A. Galindo and J. L. Teran, Tetrahedron: Asymmetry, 2004, 15, 3393
44. S. Yamauchi, S. Mori, Y. Hirai and Y. Kinoshita, Biosci., Biotechnol., Biochem., 2004, 68, 676
45. X. Wang, Y. Dong, J. Sun, X. Xu, R. Li and Y. Hu, J. Org. Chem., 2005, 70, 1897
46. L. C. Pattenden, R. A. J. Wybrow, S. A. Smith and J. P. A. Harrity, Org. Lett., 2006, 8, 3089
47. J. C. Gonzalez-Gomez, F. Foubelo and M. Yus, Synlett, 2008, 2777
48. M. E. Swarbrick and W. D. Lubell, Chirality, 2000, 12, 366
49. G. R. Proctor and F. J. Smith, J. Chem. Soc., Perkin Trans. 1, 1981, 1754
50. P. D. Bailey, R. D. Wilson and G. R. Brown, J. Chem. Soc., Perkin Trans. 1, 1991, 1337
51. P. D. Bailey, G. R. Brown, F. Korber, A. Reed and R. D. Wilson, Tetrahedron: Asymmetry, 1991, 2, 1263
52. C. Alegret, F. Santacana and A. Riera, J. Org. Chem., 2007, 72, 7688
53. J.W. Skiles, P. P. Giannousis and K. R. Fales, Bioorg. Med. Chem. Lett., 1996, 6, 963
54. P. Etayo, R. Badorrey, M. D. D?az-de-Villegas and J. A. Galvez, Synlett, 2006, 2799
55. W. E. Childers Jr. and R. B. Baudy, J. Med. Chem., 2007, 50, 2557