Organocatalytic enantioselective pictet-spengler reactions for the syntheses of 1-substituted 1,2,3,4-tetrahydroisoquinolines

Journal of Organic Chemistry

Volumn 79, Issue 16, 2014, Pages 7380-7390

  Mons, Elma ^a   Wanner, Martin J ^a   Ingemann, Steen ^a   Van Maarseveen, Jan H ^a   Hiemstra, Henk ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS;

ENANTIOMERIC PURITY; ENANTIOSELECTIVE; NATURAL PRODUCTS; ORGANOCATALYTIC; PHENYLETHYLAMINES; PICTET-SPENGLER REACTIONS; SULFENAMIDES; SYNTHETIC DRUG;

ENANTIOSELECTIVITY;

2,2' DIHYDROXY 1,1' BINAPHTHYL; ALDEHYDE; CATECHOL; NITROGEN; PHENETHYLAMINE; PHOSPHORIC ACID; TETRAHYDROISOQUINOLINE; THIOPHENOL; ACETAMIDE DERIVATIVE; ALMOREXANT; AMPA RECEPTOR; BIOLOGICAL PRODUCT; CRISPINE A; ETHYLAMINE; ISOQUINOLINE DERIVATIVE; NAPHTHOL DERIVATIVE; NITROBENZENE DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CRYSTALLIZATION; CYCLIZATION; DEBENZYLATION; DEGRADATION; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; HYDROGENOLYSIS; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILICITY; PICTET SPENGLER REACTION; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ACETAMIDES; BIOLOGICAL PRODUCTS; CATALYSIS; CYCLIZATION; ETHYLAMINES; ISOQUINOLINES; MOLECULAR STRUCTURE; NAPHTHOLS; NITROBENZENES; ORGANOPHOSPHORUS COMPOUNDS; RECEPTORS, AMPA; STEREOISOMERISM; TETRAHYDROISOQUINOLINES;

EID: 84906090791     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501099h     Document Type: Article

References (56)

1. Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341
2. Stöckigt, J.; Antonchick, A. P.; Wu, F.; Waldmann, H. Angew. Chem., Int. Ed. 2011, 50, 8538
3. Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916
4. Xie, J.-H.; Yan, P.-C.; Zhang, Q.-Q.; Yuan, K.-X.; Zhou, Q.-L. ACS Catal. 2012, 2, 561
5. Wu, Z.; Perez, M.; Scalone, M.; Ayad, T.; Ratovelomanana-Vidal, V. Angew. Chem., Int. Ed. 2013, 52, 4925
6. Chang, M.; Li, W.; Zhang, X. Angew. Chem., Int. Ed. 2011, 50, 10679
7. Iimuro, A.; Yamaji, K.; Kandula, S.; Nagano, T.; Kita, Y.; Mashima, K. Angew. Chem., Int. Ed. 2013, 52, 2046
8. Li, C.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 13208
9. Pyo, M. K.; Lee, D.-H.; Kim, D.-H.; Lee, J.-H.; Moon, J.-C.; Chang, K. C.; Yun-Choi, H. S. Bioorg. Med. Chem. Lett. 2008, 18, 4110
10. Vanden Eynden, M. J.; Stambuli, J. P. Org. Lett. 2008, 10, 5289
11. M. J. Vanden Eynden, M. J.; Kauchithapatham, K.; Stambuli, J. P. J. Org. Chem. 2010, 75, 8542
12. Pesnot, T.; Gershater, M. C.; Ward, J. M.; Hailes, H. C. Chem. Commun. 2011, 47, 3242
13. Luk, L. Y.; Bunn, S.; Liscombe, D. K.; Facchini, P. J.; Tanner, M. E. Biochemistry 2007, 46, 10153
14. Bonamore, A.; Rovardi, I.; Gasparrini, F.; Baiocco, P.; Barba, M.; Molinaro, C.; Botta, B.; Boffi, A.; Macone, A. Green Chem. 2010, 12, 1623
15. Ruff, B. M.; Bräse, S.; O'Connor, S. E. Tetrahedron Lett. 2012, 53, 1071
16. Pesnot, T.; Gershater, M. C.; Ward, J. M.; Hailes, H. C. Adv. Synth. Catal. 2012, 354, 2997
17. Klausen, R. S.; Jacobsen, E. N. Org. Lett. 2009, 11, 887
18. Lee, Y.; Klausen, R. S.; Jacobsen, E. N. Org. Lett. 2011, 13, 5564
19. Huang, D.; Xu, F.; Lin, X.; Wang, Y. Chem.-Eur. J. 2012, 18, 3148
20. Herlé, B.; Wanner, M. J.; van Maarseveen, J. H.; Hiemstra, H. J. Org. Chem. 2011, 76, 8907
21. Kerschgens, I.; Claveau, E.; Wanner, M. J.; Ingemann, S.; van Maarseveen, J. H.; Hiemstra, H. Chem. Commun. 2012, 48, 12243-7485
22. Sewgobind, N.; Wanner, M. J.; S. Ingemann, S.; de Gelder, R.; van Maarseveen, J. H.; Hiemstra, H. J. Org. Chem. 2008, 73, 6405
23. Toda, Y.; Terada, M. Synlett 2013, 752
24. Bermejo, A.; Andreu, I.; Suvire, F.; Léonce, S.; Caignard, D. H.; Renard, P.; Pierré, A.; Enriz, R. D.; Cortes, D.; Cabedo, N. J. Med. Chem. 2002, 45, 5058
25. 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
26. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3 rd ed.; Wiley: New York, 1999; pp 600-603.
27. Craine, L.; Raban, M. Chem. Rev. 1989, 89, 689
28. Wanner, M. J.; Hauwert, P.; Schoemaker, H. E.; de Gelder, R.; van Maarseveen, J. H.; Hiemstra, H. Eur. J. Org. Chem. 2008, 180
29. Szawkało, J.; Zawadzka, A.; Wojtasiewicz, K.; Leniewski, A.; Drabowicz, J.; Czarnocki, Z. Tetrahedron: Asymmetry 2005, 16, 3619
30. Wu, T. R.; Chong, J. M. J. Am. Chem. Soc. 2006, 128, 9646
31. Kanemitsu, T.; Yamashita, Y.; Nagata, K.; Itoh, T. Heterocycles 2007, 74, 199
32. Werner, F.; Blank, N.; Opatz, T. Eur. J. Org. Chem. 2007, 74, 3911
33. Szawkało, J.; Czarnocki, S. J.; Zawadzka, A.; Wojtasiewicz, K.; Leniewski, A.; Maurin, J. K.; Czarnocki, Z.; Drabowicz, J. Tetrahedron: Asymmetry 2007, 18, 406
34. Allin, S. M.; Gaskell, S. N.; Towler, J. M. R.; Page, P. C. B.; Saha, B.; McKenzie, M. J.; Martin, W. P. J. Org. Chem. 2007, 72, 8972
35. Bailey, K. R.; Ellis, A. J.; Reiss, R.; Snape, T. J.; Turner, N. J. Chem. Commun. 2007, 43, 3640
36. Hou, G.-H.; Xie, J.-H.; Yan, P.-C.; Zhou, Q.-L. J. Am. Chem. Soc. 2009, 131, 1366
37. Evanno, L.; Ormala, J.; Pihko, P. M. Chem.-Eur. J. 2009, 15, 12963
38. Miyazaki, M.; Ando, N.; Sugai, K.; Seito, Y.; Fukuoka, H.; Kanemitsu, T.; Nagata, K.; Odanaka, Y.; Nakamura, K. T.; Itoh, T. J. Org. Chem. 2011, 76, 534
39. Amat, M.; Elias, V.; Llor, N.; Subrizi, F.; Molins, E.; Bosch, J. Eur. J. Org. Chem. 2010, 4017
40. Gurram, M.; Gyimothy, B.; Wang, R.; Lam, S. Q.; Ahmed, F.; Herr, R. J. J. Org. Chem. 2011, 76, 1605
41. Louafi, F.; Moreau, J.; Shahane, S.; Golhen, S.; Roisnel, T.; Sinbandhit, S.; Hurvois, J.-P. J. Org. Chem. 2011, 76, 9720
42. Kawai, N.; Matsuda, M.; Uenishi, J. Tetrahedron 2011, 67, 8648
43. Gurram, M.; Gyimothy, B.; Wang, R.; Lam, S. Q.; Ahmed, F.; Herr, R. J. J. Org. Chem. 2011, 76, 1605
44. Sánchez-Obregón, R.; Ortiz, B.; Mastranzo, V. M.; Yuste, F.; Ruano, J. L. G. Tetrahedron Lett. 2013, 54, 1893
45. Reddy, N. S. S.; Redddy, B. J. M.; Reddy, B. V. S. Tetrahedron Lett. 2013, 54, 4228
46. Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183
47. Review: Kaufman, T. S. Synthesis 2005, 339
48. Schönstein, L.; Forró, E.; Fülöp, F. Tetrahedron: Asymmetry 2013, 24, 202
49. Tojo, E.; Önür, M. A.; Freyer, A. J.; Shamma, M. J. Nat. Prod. 1990, 53, 634
50. Reddy, R. J.; Kawai, N.; Uenishi, J. J. Org. Chem. 2012, 77, 11101
51. Huls, R.; Grégoire, E.; Nyembo, L. Bull. Soc. R. Sci. Liège 1971, 40, 203
52. Pedrosa, R.; Andrés, C.; Iglesias, J. M. J. Org. Chem. 2001, 66, 243
53. Weller, T.; Koberstein, R.; Aissaoui, H.; Clozel, M.; Fischli, W. WO 2005/118548, 2005.
54. Verzijl, G. K. M.; de Vries, A. H. M.; de Vries, J. G.; Kapitan, P.; Dax, T.; Helms, M.; Nazir, Z.; Skranc, W.; Imboden, C.; Stichler, J.; Ward, R. A.; Abele, S.; Lefort, L. Org. Process Res. Dev. 2013, 17, 1531
55. Gribkov, D. V.; Hultzsch, K. C.; Hampell, F. Chem.-Eur. J. 2003, 9, 4796
56. Liu, F.; Zha, H.-Y.; Yao, Z.-J. J. Org. Chem. 2003, 68, 6679