Asymmetric alkaloid synthesis: A one-pot organocatalytic reaction to quinolizidine derivatives

Angewandte Chemie - International Edition

Volumn 48, Issue 4, 2009, Pages 787-791

  Franzén, Johan ^a   Fisher, Andreas ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Acyliminium ion; Alkaloids; Asymmetric catalysis; Cyclization; Organocatalysis

Indexed keywords

CHEMICAL REACTIONS; CYCLIZATION; IONS; RATE CONSTANTS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ACYLIMINIUM ION; ALKALOIDS; ASYMMETRIC CATALYSIS; CHEMICAL EQUATIONS; CONJUGATE ADDITIONS; ENANTIOSELECTIVE SYNTHESES; ONE POTS; ORGANOCATALYSIS; STEREOCENTERS; TRIMETHYLSILYL;

CATALYSIS;

ALKALOID; QUINOLIZIDINE DERIVATIVE;

ARTICLE; CATALYSIS; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; CATALYSIS; QUINOLIZIDINES; STEREOISOMERISM;

EID: 58249101213     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805130     Document Type: Article

References (55)

1. a) The Alkaloids: Chemistry and Biology, Vol. 50 (Ed.: G. A. Cordell), Academic Press, New York, 1998;
2. b) C. Szántay, K. Honty in The Chemistry of Heterocyclic Compounds, Vol. 25 (Ed.: J. E. Saxton), Wiley, New York, 1994, pp. 161-216;
3. c) E. W. Baxter, P. S. Mariano in Alkaloids: Chemical and Biological Perspectives, Vol. 8 (Ed.: S. W. Pelletier), Springer, New York, 1992, pp. 197-319.
4. For reviews, see: M. Chrzanowska, M. D. Rozwadowska, Chem. Rev. 2004, 104, 3341.
5. For recent examples of quinolizidine syntheses based on starting materials from the chiral pool, see: a) A. B. Dounay, P. G. Humphreys, L. E. Oveman, A. D. Wrobleski, J. Am. Chem. Soc. 2008, 130, 5368;
6. b) M. Amat, M. M. M. Santos, O. Bassas, N. Llor, C. Escolano, A. Gómez-Esqué, E. Molins, S. M. Allin, V. McKee, J. Bosch, J. Org. Chem. 2007, 72, 5193;
7. c) J. M. Wenyuan, H. Zhou, J. M. Cook, Org. Lett. 2007, 9, 3491;
8. d) S. M. Allin, L. J. Duffy, P. C. B. Page, V. McKee, M. Edgar, M. J. McKenzie, M. Amat, O. Bassas, M. M. M. Santos, J. Bosh, Tetrahedron Lett. 2006, 47, 5713;
9. e) G. Stork, P. C. Tang, M. Casey, B. Goodman, M. Toyota, J. Am. Chem. Soc. 2005, 127, 16255;
10. f) A. Deilters, K. Chen, T. C. Eary, S. F. Martin, J. Am. Chem. Soc. 2003, 125, 4541.
11. For recent examples of quinolizidine syntheses based on asymmetric catalysis, see: a) D. J. Mergott, S. J. Zuend, E. N. Jacobsen, Org. Lett. 2008, 10, 745;
12. b) J. Szawkalo, S. J. Czarnocki, A. Zawadzka, K. Wojtasiewicz, A. Leniewski, J. K. Maurin, Z. Czarnocki, J. Drabowicz, Tetrahedron: Asymmetry 2007, 18, 406;
13. c) T. R. Wu, J. M. Chong, J. Am. Chem. Soc. 2006, 128, 9646;
14. d) L. S. Santos, R. A. Pilli, V. H. Rawal, J. Org. Chem. 2004, 69, 1283;
15. e) C. K. Jana, A. Studer, Chem. Eur. J. 2008, 14, 6326.
16. For organocatalytic approaches to give indoloquinolizidine derivatives, see: a) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2006, 8, 1533;
17. b) K. Frisch, A. Landa, S. Saaby, K. A. Jørgensen, Angew. Chem. 2005, 117, 6212;
18. Angew. Chem. Int. Ed. 2005, 44, 6058.
19. For an excellent non-asymmetric cascade reaction to give quinolizidine derivatives, see: A. W. Pilling, J. Boehmer, D. J. Dixon, Angew. Chem. 2007, 119, 5524;
20. Angew. Chem. Int. Ed. 2007, 46, 5428.
21. For recent reviews on organocatalysis, see: a) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716;
22. Angew. Chem. Int. Ed. 2008, 47, 4638;
23. b) Chem. Rev. 2007, 107(12).
24. Special edition devoted to asymmetric organocatalysis; c) P. L. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
25. Angew. Chem. Int. Ed. 2004, 43, 5138;
26. d) A. Berkessel, H. Grger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2004.
27. For recent reviews on organocatalytic conjugate addition, see: a) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701;
28. b) A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416.
29. For reviews, see: a) B. E. Maryanoff, H. Zhang, J. H. Cohen, I. J. Turchi, C. A. Maryanoff, Chem. Rev. 2004, 104, 1431;
30. b) J. Royer, M. Bonin, L. Micouin, Chem. Rev. 2004, 104, 2311.
31. For recent examples of asymmetric cyclizations of the acyliminium ion, see: a) I. T. Raheem, P. S. Thiara, E. A. Peterson, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 13404;
32. b) M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 10558.
33. a) S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411;
34. Angew. Chem. Int. Ed. 2006, 45, 4305;
35. b) A. Carlone, S. Cabrera, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 1119;
36. Angew. Chem. Int. Ed. 2007, 46, 1101;
37. c) M. Marigo, S. Bertelsen, A. Landa, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 5475;
38. d) A. Carlone, M. Marigo, C. North, A. Landa, K. A. Jørgensen, Chem. Commun. 2006, 4928;
39. e) L. Zu, H. Xie, H. Li, J. Wang, X. Yu, W. Wang, Chem. Eur. J. 2008, 14, 6333.
40. a) K. R. Knudsen, C. E. T. Mitchell, S. V. Ley, Chem. Commun. 2006, 66;
41. b) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2004, 116, 1292;
42. Angew. Chem. Int. Ed. 2004, 43, 1272;
43. c) N. Halland, T. Hansen, K. A. Jørgensen, Angew. Chem. 2003, 115, 5105;
44. Angew. Chem. Int. Ed. 2003, 42, 4955;
45. d) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685;
46. Angew. Chem. Int. Ed. 2003, 42, 661;
47. e) N. Halland, K. A. Jørgensen, T. Hansen, WO 03/050105, 2003.
48. The diastereomeric mixtures 3/4 and 5/6 could be separated by flash column chromatography (see the Supporting Information).
49. 2O) was used, only the corresponding hemiacetal 9 was isolated.
50. CCDC 705562 (5 f) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
51. B. E. Maryanoff, D. F. McComsey, B. A. Duhl-Emswiler, J. Org. Chem. 1983, 48, 5062.
52. a) M. Lounasmaa, M. Berner, M. Brunner, H. Suomalainen, A. Tolvanen, Tetrahedron 1998, 54, 10205;
53. b) M. Node, H. Nagasawa, K. Fuji, J. Am. Chem. Soc. 1987, 109, 7901;
54. c) M. Lounasmaa, M. Berner, A. Tolvanen, Heterocycles 1998, 48, 1275.
55. 1H NMR spectra, see the Supporting Information.