Enantioselective Brønsted acid-catalyzed N-acyliminium cyclization cascades

Journal of the American Chemical Society

Volumn 131, Issue 31, 2009, Pages 10796-10797

  Muratore, Michael E ^a,b   Holloway, Chloe A ^a   Pilling, Adam W ^a   Storer, R Ian ^c   Trevitt, Graham ^d   Dixon, Darren J ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^d UCB Celltech   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CYCLIZATION REACTIONS; CYCLOISOMERIZATIONS; DIASTEREO- AND ENANTIOSELECTIVITY; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; ENOL LACTONES; HETEROCYCLES; HIGH ENANTIOSELECTIVITY; IN-SITU; N-ACYLIMINIUM CYCLIZATION; REACTION PARTNERS; TRYPTAMINES;

ACIDS; ENANTIOSELECTIVITY; GOLD COMPOUNDS; PHOSPHORIC ACID; TOLUENE;

CYCLIZATION;

ALKYNE DERIVATIVE; BRONSTED ACID; ELECTROPHILE; GOLD; LACTONE DERIVATIVE; PHOSPHORIC ACID; TOLUENE; TRYPTAMINE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; LACTONES; ORGANIC CHEMISTRY PROCESSES; STEREOISOMERISM; TRYPTAMINES;

EID: 68249145925     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9024885     Document Type: Article

References (43)

1. For reviews, see: (a) Maryanoff, B. E.; Zhang, H. C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431.
2. (b) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
3. (c) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
4. For selected reviews, see: (a) Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
5. (b) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134.
6. (c) Tietze, L. F. Chem. Rev. 1996, 96, 115.
7. (a) Yang, T.; Campbell, L.; Dixon, D. J. J. Am. Chem. Soc. 2007, 129, 12070.
8. Also see: (b) Yang, T.; Ferrali, A.; Campbell, L.; Dixon, D. J. Chem. Commun. 2008, 2923.
9. For pioneering studies on chiral phosphoric acid catalysis, see: (a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.
10. (b) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
11. For recent reviews on asymmetric organocatalysis by H-bond donors and Brønsted acids, see: (a) Akiyama, T. Chem. Rev. 2007, 107, 5744.
12. (b) Doyle, A.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713.
13. (c) Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999.
14. For selected examples illustrating the high levels of enantioselectivity using chiral Brønsted acid organocatalysis, see: (a) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84.
15. (b) Martin, N. J. A.; Ozores, L.; List, B. J. Am. Chem. Soc. 2007, 129, 8976.
16. (c) Itoh, J.; Fuchibe, K.; Akiyama, T. Angew. Chem., Int. Ed. 2008, 47, 4016.
17. (d) Terada, M.; Soga, K.; Momiyama, N. Angew. Chem., Int. Ed. 2008, 47, 4122.
18. (e) Rueping, M.; Theissmann, T.; Raja, S.; Bats, J. W. Adv. Synth. Catal. 2008, 350, 1001.
19. (f) Kang, Q.; Zheng, X.-J.; You, S.-L. Chem. - Eur. J. 2008, 14, 3539.
20. (g) Rowland, G. B.; Rowland, E. B.; Liang, Y.; Perman, J. A.; Antilla, J. C. Org. Lett. 2007, 9, 2609.
21. For examples of the related asymmetric Pictet-Spengler reaction under chiral Brønsted acid catalysis, see: (a) Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, 128, 1086.
22. (b) Mergott, D. J.; Zuend, S. J.; Jacobsen, E. N. Org. Lett. 2008, 10, 745.
23. (c) Wanner, M. J.; van der Haas, R. N. S.; de Cuba, K. R.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2007, 46, 7485.
24. (d) Sewgobind, N. V.; Wanner, M. J.; Ingemann, S.; de Gelder, R.; van Maarseveen, J. H.; Hiemstra, H. J. Org. Chem. 2008, 73, 6405.
25. For a thiourea-catalyzed example, see: (e) Klausen, R. S.; Jacobsen, E. N. Org. Lett. 2009, 11, 887.
26. For examples of N-acyliminium cyclizations using chiral thiourea catalysts, see: (a) Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404.
27. (b) Raheem, I. T.; Thiara, P. S.; Jacobsen, E. N. Org. Lett. 2008, 10, 1577.
28. For examples of chiral counterion-mediated asymmetric catalysis, see: (a) García-García, P.; Lay, F.; García-García, P.; Rabalakos, C.; List, B. Angew. Chem., Int. Ed. 2009, 48, 4363.
29. (b) Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496.
30. (c) Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336.
31. (d) Rueping, M.; Antonchick, A. P.; Brickmann, C. Angew. Chem., Int. Ed. 2007, 46, 6903.
32. For discussions of dynamic kinetic asymmetric transformations, see: (a) Steinreiber, J.; Faber, K.; Griengl, H. Chem. - Eur. J. 2008, 14, 8060.
33. See also: (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 3543.
34. The same diastereoisomer is the sole reaction product using PTSA (cat).
35. For selected examples of tandem (or dual) metal/organocatalysis, see: (a) Chercheja, S.; Rothenbücher, R.; Eilbracht, P. Adv. Synth. Catal. 2009, 351, 339.
36. (b) Han, Z.-Y.; Xiao, H.; Chen, X.-H.; Gong, L.-H. J. Am. Chem. Soc. 2009, 131, 9182.
37. (c) Terada, M.; Toda, Y. J. Am. Chem. Soc. 2009, 131, 6954.
38. (d) Hu, W.; Xu, X.; Zhou, J.; Liu, W.-J.; Huang, H.; Hu, J.; Yang, L.; Gong, L.-Z. J. Am. Chem. Soc. 2008, 130, 7782.
39. (e) Sorimashi, K.; Terada, M. J. Am. Chem. Soc. 2008, 130, 14452.
40. (f) Ref 9d.
41. (g) Ref 9c.
42. (h) Komanduri, V.; Krische, M. P. J. Am. Chem. Soc. 2006, 128, 16448.
43. 3 gave 5d in 11% yield and 75% ee.