Highly enantioselective pictet-spengler reaction catalyzed by SPINOL-phosphoric acids

Chemistry - A European Journal

Volumn 18, Issue 11, 2012, Pages 3148-3152

  Huang, Dan ^a   Xu, Fangxi ^a   Lin, Xufeng ^a   Wang, Yanguang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

heterocycles; organocatalysis; phosphoric acids; Pictet Spengler reaction; tryptamines

Indexed keywords

AROMATIC ALDEHYDE; ASYMMETRIC TOTAL SYNTHESIS; CARBOLINES; ENANTIOSELECTIVE; ENANTIOSELECTIVE CATALYSTS; HETEROCYCLES; OPTICALLY ACTIVE; ORGANOCATALYSIS; PICTET-SPENGLER REACTIONS; TRYPTAMINES;

ALDEHYDES; CATALYSIS; PHOSPHORIC ACID; REACTION KINETICS;

ENANTIOSELECTIVITY;

EID: 84863230357     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103207     Document Type: Article

References (49)

1. E. D. Cox, J. M. Cook, Chem. Rev. 1995, 95, 1797-1842
2. M. Somei, F. Yamada, Nat. Prod. Rep. 2004, 21, 278-311
3. T. Kawasaki, K. Higuchi, Nat. Prod. Rep. 2005, 22, 761-793
4. S. E. O'Connor, J. J. Maresh, Nat. Prod. Rep. 2006, 23, 532-547
5. Y.-C. Shen, C.-Y. Chen, P.-W. Hsieh, C.-Y. Duh, Y.-M. Lin, C.-L. Ko, Chem. Pharm. Bull. 2005, 53, 32-36.
6. A. Daugan, P. Grondin, C. Ruault, A.-C. Le Monnier de Gouvill, H. Coste, J. Kirilovsky, F. Hyafil, R. Labaudinière, J. Med. Chem. 2003, 46, 4525-4532.
7. M. Lorenz, M. L. Van Linn, J. M. Cook, Curr. Org. Synth. 2010, 7, 189-223
8. J. Stöckigt, A. P. Antonchick, F. Wu, H. Waldmann, Angew. Chem. 2011, 123, 8692-8719
9. Angew. Chem. Int. Ed. 2011, 50, 8538-8564; for selected examples of asymmetric catalytic Pictet-Spengler reactions, see
10. M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 10558-10559
11. R. S. Klausen, E. N. Jacobsen, Org. Lett. 2009, 11, 887-890
12. J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc. 2006, 128, 1086-1087
13. M. J. Wanner, R. N. S. van der Haas, K. R. de Cuba, J. H. van Maarseveen, H. Hiemstra, Angew. Chem. 2007, 119, 7629-7631
14. Angew. Chem. Int. Ed. 2007, 46, 7485-7487
15. N. V. Sewgobind, M. J. Wanner, S. Ingemann, R. de Gelder, J. H. van Maarseveen, H. Hiemstra, J. Org. Chem. 2008, 73, 6405-6408
16. M. E. Muratore, C. A. Holloway, A. W. Pilling, R. I. Storer, G. Trevitt, D. J. Dixon, J. Am. Chem. Soc. 2009, 131, 10796-10797
17. M. J. Wanner, R. N. A. Boots, B. Eradus, R. de Gelder, J. H. van Maarseveen, H. Hiemstra, Org. Lett. 2009, 11, 2579-2581
18. S. Duce, F. Pesciaioli, L. Gramigna, L. Bernardi, A. Mazzanti, A. Ricci, G. Bartoli, G. Bencivenni, Adv. Synth. Catal. 2011, 353, 860-864.
19. T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594
20. Angew. Chem. Int. Ed. 2004, 43, 1566-1568
21. D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357; for VAPOL-derived phosphoric acids, see
22. G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla, J. Am. Chem. Soc. 2005, 127, 15696-15697; for TADDOL-derived phosphoric acids, see
23. T. Akiyama, Y. Saitoh, H. Morita, K. Fuchibe, Adv. Synth. Catal. 2005, 347, 1523-1526 for recent reviews on chiral Brønsted acid and hydrogen-bond-donor catalysis, see
24. M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573
25. Angew. Chem. Int. Ed. 2006, 45, 1520-1543
26. T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999-1010
27. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743
28. T. Akiyama, Chem. Rev. 2007, 107, 5744-5758
29. M. Terada, Chem. Commun. 2008, 4097-4112
30. X. H. Yu, W. Wang, Chem. Asian J. 2008, 3, 516-532
31. M. Terada, Synthesis 2010, 1929-1982
32. A. Zamfir, S. Schenker, M. Freund, S. B. Tsogoeva, Org. Biomol. Chem. 2010, 8, 5262-5276
33. M. Rueping, A. Kuenkel, I. Atodiresei, Chem. Soc. Rev. 2011, 40, 4539-4549
34. H. Yamamoto, N. Payette, in Hydrogen Bonding in Organic Synthesis (Ed.:, P. M. Pihko,), WileyVCH, Weinheim, 2009, Chapter 5, pp. 73-140
35. D. Kampen, C. M. Reisinger, B. List, in Topics in Current Chemistry, Vol. 291: Asymmetric Organocatalysis (Ed.:, B. List,), Springer, Berlin, 2010, pp. 395-456.
36. F. X. Xu, D. Huang, C. Han, W. Shen, X. F. Lin, Y. G. Wang, J. Org. Chem. 2010, 75, 8677-8680.
37. I. Čorić, S. Müller, B. List, J. Am. Chem. Soc. 2010, 132, 17370-17373
38. S. Müller, M. J. Webber, B. List, J. Am. Chem. Soc. 2011, 133, 18534-18537.
39. C. H. Xing, Y. X. Liao, J. Ng, Q. S. Hu, J. Org. Chem. 2011, 76, 4125-4131.
40. B. Xu, S. F. Zhu, X. L. Xie, J. J. Shen, Q. L. Zhou, Angew. Chem. 2011, 123, 11685-11688
41. Angew. Chem. Int. Ed. 2011, 50, 11483-11486.
42. N. Kakinuma, H. Iwai, S. Takahashi, K. Hamano, T. Yanagisawa, K. Nagai, K. Tanaka, K. Suzuki, F. Kirikae, T. Kirikae, A. Nakagawa, J. Antibiot. 2000, 53, 1247-1251
43. S. Takahashi, N. Kakinuma, H. Iwai, T. Yanagisawa, K. Nagai, K. Suzuki, T. Tokunaga, A. Nakagawa, J. Antibiot. 2000, 53, 1252-1256
44. X. Q. Zhang, W. Q. Jiang, Z. H. Sui, J. Org. Chem. 2003, 68, 4523-4526.
45. T.-S. Kam, K.-M. Sim, Phytochemistry 1998, 47, 145-147; for examples of the total synthesis of harmicine, see
46. T. Itoh, M. Miyazaki, K. Nagata, M. Yokoya, S. Nakamura, A. Ohsawa, Heterocycles 2002, 58, 115-118
47. J. Szawkało, S. J. Czarnocki, A. Zawadzka, K. Wojtasiewicz, A. Leniewski, J. K. Maurin, Z. Czarnocki, J. Drabowicz, Tetrahedron: Asymmetry 2007, 18, 406-413
48. I. T. Raheem, P. S. Thiara, E. A. Peterson, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 13404-13405
49. W. A. da Silva, M. T. Rodrigues, Jr., N. Shankaraiah, R. B. Ferreira, C. K. Z. Andrade, R. A. Pilli, L. S. Santos, Org. Lett. 2009, 11, 3238-3241.