A Titanium(III)-Catalyzed Reductive Umpolung Reaction for the Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines

Organic Letters

Volumn 17, Issue 10, 2015, Pages 2478-2481

  Luu, Hieu Trinh ^a   Wiesler, Stefan ^a   Frey, Georg ^a   Streuff, Jan ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3-DEMETHOXYERYTHRATIDINONE; INDOLE ALKALOID; NITRILE; TETRAHYDROISOQUINOLINE DERIVATIVE; TITANIUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; NITRILES; STEREOISOMERISM; TETRAHYDROISOQUINOLINES; TITANIUM;

EID: 84929589839     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00987     Document Type: Article

References (67)

1. The Chemistry and Biology of Isoquinoline Alkaloids; Phillipson, J. D., Roberts, M. F., Zenk, M. H., Eds.; Springer: Berlin, 2012.
2. Bentley, K. W. Isoquinoline Alkaloids; CRC Press (Taylor & Francis): Boca Raton, 1998.
3. Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341 - 3370
4. DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094 - 8097
5. Parsons, A. F.; Palframan, M. J. Erythrina and related Alkaloids. In The Alkaloids: Chemistry and Biology, Vol. 68; Cordell, G. A., Ed.; Elsevier: Amsterdam, 2010; pp 39 - 81.
6. Preisner, R. M.; Shamma, M. J. Nat. Prod. 1980, 43, 305 - 318
7. Hodgkiss, J. P.; Sherriffs, H. J.; Cottrell, D. A.; Shirakawa, K.; Kelly, J. S.; Kuno, A.; Ohkubo, M.; Butcher, S. P.; Olverman, H. J. Eur. J. Pharmacol. 1993, 240, 219 - 227
8. Wong, E. H. F.; Kemp, J. A.; Priestley, T.; Knight, A. R.; Woodruff, G. N.; Iversen, L. L. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 7104 - 7108
9. Anderson, P.; Christy; Evans, B. E. (Merck & Co., Inc.), U.S. Patent 4,399,141, 1983.
10. Eynden, M. J. V.; Kunchithapatham, K.; Stambuli, J. P. J. Org. Chem. 2010, 75, 8542 - 8549
11. Hegedüs, A.; Hell, Z. Tetrahedron Lett. 2004, 45, 8553 - 8555
12. Venkov, A. P.; Angelov, P. A. Synth. Commun. 2003, 33, 3025 - 3033
13. Horiguchi, Y.; Kodama, H.; Nakamura, M.; Yoshimura, T.; Hanezi, K.; Hamada, H.; Saitoh, T.; Sano, T. Chem. Pharm. Bull. 2002, 50, 253 - 257
14. Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552 - 6554
15. Tietze, L. F.; Tölle, N.; Kratzert, D.; Stalke, D. Org. Lett. 2009, 11, 5230 - 5233
16. Bialy, S. A. A. E.; Braun, H.; Tietze, L. F. Angew. Chem., Int. Ed. 2004, 43, 5391 - 5393
17. Li, X.; Coldham, I. J. Am. Chem. Soc. 2014, 136, 5551 - 5554
18. Muramatsu, W.; Nakano, K.; Li, C.-J. Org. Biomol. Chem. 2014, 12, 2189 - 2192
19. Shirakawa, S.; Liu, K.; Ito, H.; Le, T. N.; Maruoka, K. Adv. Synth. Catal. 2011, 353, 2614 - 2618
20. Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784 - 10785
21. Meyers, A. I.; Du, B.; Gonzalez, M. A. J. Org. Chem. 1990, 55, 4218 - 4220
22. Lohmann, J.-J.; Seebach, D.; Syfrig, M. A.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1981, 20, 128 - 129
23. Shamma, M.; Jones, C. D. J. Org. Chem. 1970, 35, 3119 - 3121
24. Rossi, B.; Prosperini, S.; Pastori, N.; Clerici, A.; Punta, C. Molecules 2012, 17, 14700 - 14732
25. Gansäuer, A.; Fan, C.-A.; Keller, F.; Karbaum, P. Chem.-Eur. J. 2007, 13, 8084 - 8090
26. Gansäuer, A.; Justicia, J.; Fan, C.-A.; Worgull, D.; Piestert, F. Top. Curr. Chem. 2007, 279, 25 - 52
27. Gansäuer, A.; Kube, C.; Daasbjerg, K.; Sure, R.; Grimme, S.; Fianu, G. D.; Sadasivam, D. V.; Flowers, R. A., II. J. Am. Chem. Soc. 2014, 136, 1663 - 1671
28. Gansäuer, A.; Behlendorf, M.; von Laufenberg, D.; Fleckhaus, A.; Kube, C.; Sadasivam, D. V.; Flowers, R. A., II. Angew. Chem., Int. Ed. 2012, 51, 4739 - 4742
29. Gansäuer, A.; Klatte, M.; Brändle, G. M.; Friedrich, J. Angew. Chem., Int. Ed. 2012, 51, 8891 - 8894
30. Gansäuer, A.; Otte, M.; Shi, L. J. Am. Chem. Soc. 2011, 133, 416 - 417
31. Streuff, J. Synthesis 2013, 45, 281 - 307
32. Hirao, T. Top. Curr. Chem. 2007, 279, 53 - 75
33. Gansäuer, A.; Bluhm, H. Chem. Rev. 2000, 100, 2771 - 2788
34. Streuff, J. Chem. Rec. 2014, 14, 1100 - 1113
35. Bichovski, P.; Haas, T. M.; Kratzert, D.; Streuff, J. Chem.-Eur. J. 2015, 21, 2339 - 2342
36. Feurer, M.; Frey, G.; Luu, H.-T.; Kratzert, D.; Streuff, J. Chem. Commun. 2014, 50, 5370 - 5372
37. Frey, G.; Luu, H.-T.; Bichovski, P.; Feurer, M.; Streuff, J. Angew. Chem., Int. Ed. 2013, 52, 7131 - 7134
38. Streuff, J.; Feurer, M.; Bichovski, P.; Frey, G.; Gellrich, U. Angew. Chem., Int. Ed. 2012, 51, 8661 - 8664
39. Streuff, J. Chem.-Eur. J. 2011, 17, 5507 - 5510
40. Paradas, M.; Campaña, A. G.; Estévez, R. E.; Álvarez de Cienfuegos, L.; Jiménez, T.; Robles, R.; Cuerva, J. M.; Oltra, J. E. J. Org. Chem. 2009, 74, 3616 - 3619
41. Yamamoto, Y.; Hattori, R.; Itoh, K. Chem. Commun. 1999, 825 - 826
42. Gansäuer, A.; Bauer, D. Eur. J. Org. Chem. 1998, 2673 - 2676
43. Gansäuer, A.; Moschioni, M.; Bauer, D. Eur. J. Org. Chem. 1998, 1923 - 1927
44. Gansäuer, A. Synlett 1997, 363 - 364
45. Gansäuer, A. Chem. Commun. 1997, 457 - 458
46. Gansäuer, A.; Piestert, F.; Huth, I.; Lauterbach, T. Synthesis 2008, 3509 - 3515
47. Fernández-Mateos, A.; Herrero Teijón, P.; Mateos Burón, L.; Rabanedo Clemente, R.; Rubio González, R. J. Org. Chem. 2007, 72, 9973 - 9982
48. Fernández-Mateos, A.; Mateos Burón, L.; Rabanedo Clemente, R.; Ramos Silvo, A. I.; Rubio González, R. Synlett 2004, 1011 - 1014
49. Yamamoto, Y.; Matsumi, D.; Hattori, R.; Itoh, K. J. Org. Chem. 1999, 64, 3224 - 3229
50. Yamamoto, Y.; Matsumi, D.; Itoh, K. Chem. Commun. 1998, 875 - 876
51. See Supporting Information.
52. An asymmetric variant was attempted during our initial screening experiments, and several chiral titanocene catalysts were tested. The highest enantioselectivity was achieved with (R, R)-(ebthi)TiCl2 as the catalyst (17% ee).
53. Heller, S. T.; Kiho, T.; Narayan, A. R. H.; Sarpong, R. Angew. Chem., Int. Ed. 2013, 52, 11129 - 11133
54. Chuang, K. V.; Navarro, R.; Reisman, S. E. Chem. Sci. 2011, 2, 1086 - 1089
55. Joo, J. M.; David, R. A.; Yuan, Y.; Lee, C. Org. Lett. 2010, 12, 5704 - 5707
56. Zhang, F.; Simpkins, N. S.; Blake, A. J. Org. Biomol. Chem. 2009, 7, 1963 - 1979
57. Wang, Q.; Padwa, A. Org. Lett. 2006, 8, 601 - 604
58. Allin, S. M.; Streetley, G. B.; Slater, M.; James, S. L.; Martin, W. P. Tetrahedron Lett. 2004, 45, 5493 - 5496
59. Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron Lett. 1998, 39, 8995 - 8998
60. Wasserman, H. H.; Amici, R. M. J. Org. Chem. 1989, 54, 5843 - 5844
61. Danishefsky, S. J.; Panek, J. S. J. Am. Chem. Soc. 1987, 109, 917 - 918
62. Tanaka, H.; Shibata, M.; Ito, K. Chem. Pharm. Bull. 1984, 32, 1578 - 1582
63. Bischler, A.; Napieralski, B. Ber. Dtsch. Chem. Ges. 1893, 26, 1903 - 1908
64. Li, W.-D. Z.; Wang, Y.-Q. Org. Lett. 2003, 5, 2931 - 2934
65. Miller, D. G.; Wayner, D. D. M. J. Org. Chem. 1990, 55, 2924 - 2927
66. Typical solvents such as DMF or 1,4-dioxane were not suitable.
67. Good yields required the use of degassed methanol.