Synthesis of an enantiocomplementary catalyst of β-isocupreidine (β-ICD) from quinine

Advanced Synthesis and Catalysis

Volumn 347, Issue 14, 2005, Pages 1790-1796

  Nakano, Ayako ^a   Ushiyama, Mina ^a   Iwabuchi, Yoshiharu ^a   Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

isocupreidine; Asymmetric catalysis; Baylis Hillman reaction; Organic catalysis; Quinine

Indexed keywords

EID: 28244486933     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505138     Document Type: Article

References (24)

1. a) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811-892;
2. b) Y. Iwabuchi, S, Hatakeyama, J. Synth. Org. Chem. Jpn. 2002, 60, 4-16;
3. c) P. Langer, Angew. Chem. Int. Ed. 2000, 39, 3049-3052;
4. d) E. Ciganek in: Organic Reactions, Vol. 51 (Ed.: L. A. Paquette), Wiley, New York, 1997, pp. 201-350;
5. e) D. Basavaiah, P. Darma Rao, R. Suguna Hyma, Tetrahedron 1996, 52, 8001-8062;
6. S. E. Drewes, G. H. P. Roos, Tetrahedron 1988, 44, 4653-4670.
7. Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219-10220.
8. S. Kawahara, A. Nakano, T. Esumi, Y. Iwabuchi, S. Hatakeyama, Org. Lett. 2003, 5, 3103-3105.
9. a) C. von Riesen, H. M. R. Hoffmann, Chem. Eur. J. 1996, 2, 680-684;
10. b) W. Braje, J. Frackenpohl, P. Langer, H. M. R. Hoffmann, Tetrahedron 1998, 54, 3495-3512.
11. For other works using β-ICD, see: a) M. Shi, Y.-M. Xu, Y.-L. Shi, Chem. Eur. J. 2005, 11, 1794-1802;
12. b) S. Saaby, M. Bella, K. A. Jorgensen J. Am. Chem. Soc. 2004, 126, 8120-8121;
13. c) D. Balan, H. Adolfsson, Tetrahedron Lett. 2003, 44, 2521-2524;
14. d) M. Shi, Y.-M. Xu, Angew. Chem. Int. Ed. 2002, 41, 4507-4510.
15. a) Y. Iwabuchi, M. Furukawa, T. Esumi, S. Hatakeyama, Chem. Commun. 2001, 2030-2031;
16. b) Y. Iwabuchi, T. Sugihara, T. Esumi, S. Hatakeyama, Tetrahedron Lett. 2001, 42, 7867-7871.
17. Recently, an asymmetric synthesis of (+)-quinidine was reported by Jacobsen et al. This method can be applied to the synthesis of (-)-quinidine, which is required for the preparation of the enantiomer of β-ICD: I. T. Raheem, S. N. Goodman, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 706-707.
18. D. H. R. Barton, J. M. Beaton, L. E. Geller, M. M. Pechet, J. Am. Chem. Soc. 1961, #83#86, 4076-4083.
19. L. P. Stotter, K. A. Hill, M. D. Friedman, Heterocycles 1987, 25, 259-262.
20. F. Asinger, B. Fell, P. Krings, Tetrahedron Lett. 1966, 633-641.
21. G. W. Kabalka, H. C. Jr. Hedgecock, J. Org. Chem. 1975, 40, 1976-1979.
22. N. A. Poter, S. E. Caldwell, J. R. Lowe, J. Org. Chem. 1998, 63, 5547-5554.
23. E. Wildsmith, G. H. Timms, Tetrahedron Lett. 1971, 195-198.
24. D. H. R. Barton, S. W. McCombie, J. Chem. Soc. Perkin Trans. 1 1975, 1574-1585.