Organocatalytic diastereo- and enantioselective annulation reactions - Construction of optically active 1,2-dihydroisoquinoline and 1,2-dihydrophthalazine derivatives

Angewandte Chemie - International Edition

Volumn 44, Issue 37, 2005, Pages 6058-6063

  Frisch, Kim ^a   Landa, Aitor ^a   Saaby, Steen ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Annulation; Isoquinolines; Nitrogen heterocycles; Organocatalysis; Phthalazines

Indexed keywords

CATALYSIS; NITROGEN; STEREOCHEMISTRY;

ANNULATION; ISOQINOLINE; NITROGEN HETEROCYCLES; ORGANICATALYSIS; PHTHALAZINES;

AROMATIC COMPOUNDS;

1,2 DIHYDROPHTHALAZINE; 1,2-DIHYDROPHTHALAZINE; G 1617; ISOQUINOLINE DERIVATIVE; PHTHALAZINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; ISOQUINOLINES; MOLECULAR STRUCTURE; PHTHALAZINES; STEREOISOMERISM;

EID: 25144451926     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501900     Document Type: Article

References (81)

1. a) K. W. Bentley, The Isoquinoline Alkaloids. 1st ed., Pergamon, London, 1965;
2. b) K. W. Bentley, Nat. Prod. Rep. 2001, 18, 148;
3. c) J. P. Michael, Nat. Prod. Rep. 2002, 19, 742, and references therein;
4. d) J. D. Scott, R. M. Williams, Chem. Rev. 2002, 102, 1669;
5. e) Comprehensive Medicinal Chemistry, Vol. 3, 1st ed. (Eds.: C. Mansch, P. G. Sammes, J. B. Taylor), Pergamon, Oxford, 1990.
6. For example, see: a) E. Pop, W.-M. Wu, E. Shek, N. Bodor, J. Med. Chem. 1989, 32, 1774;
7. b) M. M. Sheha, N. A. El-Koussi, H. Farag, Arch. Pharm. Pharm. Med. Chem. 2003, 1, 47;
8. c) S. Mahmoud, T. Aboul-Fadl, H. Farag, A.-M. I. Mouhamed, Arch. Pharm. Pharm. Med. Chem. 2003, 336, 573;
9. d) L. Prokai, K. Prokai-Tatrai, N. Bodor, Med. Res. Rev. 2000, 20, 367.
10. E. Lukevics, I. Segal, A. Zablotskaya, S. Germane, Molecules 1997, 2, 180.
11. a) B. E. Maryanoff, D. F. McComsey, J. F. Gardocki, R. P. Shank, M. J. Costanzo, S. O. Nortey, C. R. Schneider, P. E. Setler, J. Med. Chem. 1987, 30, 1433;
12. b) K. L. Sorgi, C. A. Maryanoff, D. F. McComsey, D. W. Graden, B. E. Maryanoff, J. Am. Chem. Soc. 1990, 112, 3567.
13. a) L. F. Tietze, N. Rackehmann, I. Müller, Chem. Eur. J. 2004, 10, 2722, and references therein;
14. b) H.-J. Knölker, S. Agarwal, Tetrahedron Lett. 2005, 46, 1173, and references therein.
15. a) M. Chrzanowska, M. D. Rozwadowska, Chem. Rev. 2004, 104, 3341;
16. b) A. I. Meyers, D. A. Dickman, M. Boes, Tetrahedron 1987, 43, 5095;
17. c) J. Royer, M. Bonin, L. Micouin, Chem. Rev. 2004, 104, 2311.
18. For example, see: a) N. Cabedo, I. Andreu, M. C. Ramirez-de Arellano, A. Chagraoui, A. Serrano, A. Bermejo, P. Protais, D. Cortes, J. Med. Chem. 2001, 44, 1794;
19. b) T. Itoh, K. Nagata, M. Miyazaki, K. Kameoka, A. Ohsawa, Tetrahedron 2001, 57, 8827;
20. c) J.-J. Youte, D. Barbier, A. Al-Mourabit, D. Gnecco, C. Marazano, J. Org. Chem. 2004, 69, 2737;
21. d) D. Barbier, C. Marazano, C. Riche, B. C. Das, P. Potier, J. Org. Chem. 1998, 63, 1767;
22. e) M. Takamura, K. Funabashi, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6327;
23. f) M. Takamura, K. Funabashi, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 6801;
24. g) K. Funabashi, H. Ratni, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 10784;
25. h) O. Sieck, M. Ehwald, J. Liebscher, Eur. J. Org. Chem. 2005, 663.
26. a) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133;
27. b) T. Ooi, M. Takeuchi, K. Maruoka, Synthesis 2001, 1716;
28. c) K. Ho, S. Akashi, B. Saito, T. Katsuki, Synlett 2003, 1809;
29. d) M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 10558.
30. For example, see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
31. Angew. Chem. Int. Ed. 2004, 43, 5138;
32. b) A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2004;
33. c) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719.
34. For example, see: Mannich reaction: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336;
35. b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827;
36. c) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866;
37. d) A. Córdova, Acc. Chem. Res. 2004, 37, 102;
38. aldol: e) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395;
39. f) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260;
40. g) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798,
41. amination: h) B. List, J. Am. Chem. Soc. 2002, 124, 5656;
42. i) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868;
43. Angew. Chem. Int. Ed. 2002, 41, 1790;
44. j) N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Bøgevig, K. A. Jørgensen, J. Am. Chem. Soc. 2002, 124, 6254;
45. aminoxylation/hydroxylation: k) G. Zhong, Angew. Chem. 2003, 115, 4379;
46. Angew. Chem. Int. Ed. 2003, 42, 4247;
47. l) S. P. Brown, M. P. Brochu, C. J. Sinz, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 10808;
48. m) H. Sundén, M. Engqvist, J. Casas, I. Ibrahem, A. Córdova, Angew. Chem. 2004, 116, 6532;
49. Angew. Chem. Int. Ed. 2004, 43, 6694;
50. chlorination: n) M. P. Brochu, S. P. Brown, D. W. C. MacMillan, J. Am. Chem. Soc. 2004, 126, 4108;
51. o) N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 4790;
52. p) M. Marigo, S. Bachmann, N. Halland, A. Braunton, K. A. Jørgensen, Angew. Chem. 2004, 116, 5623;
53. Angew. Chem. Int. Ed. 2004, 43, 5507;
54. sulfenylation : q) M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804;
55. Angew. Chem. Int. Ed. 2005, 44, 794;
56. fluorination: r) M. Marigo, D. Fielenbach, A. Braunton, A. Kjærgaard, K. A. Jørgensen, Angew. Chem. 2005, 117, 3769;
57. Angew. Chem. Int. Ed. 2005, 44, 3703;
58. s) D. D. Steiner, N. Mase, C. F. Barbas III, Angew. Chem. Int. Ed. 2005, 117, 3772;
59. Angew. Chem. Int. Ed. 2005, 44, 3706;
60. t) T. D. Beeson, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 8826.
61. For example, see: a) A. Reissert, Ber. Dtsch. Chem. Ges. 1905, 38, 1603;
62. b) K.-Y. Akiba, K. Araki, M. Nakatani, M. Wada, Tetrahedron Lett. 1981, 22, 49, 4961;
63. c) K.-Y. Akiba, M. Nakatani, M. Wada; Y. Yamamoto, J. Org. Chem. 1985, 50, 63;
64. d) A. Dondoni, T. Dall'Occo, G. Galliani, A. Mastellari, F. Medici, Tetrahedron Lett. 1984, 25, 3637;
65. e) R. Yamaguchi, B. Hatano, T. Nakayasu, S. Kozima, Tetrahedron Lett. 1997, 38, 403;
66. f) L. N. Babichenko, A. A. Tolmachev, T. S. Chmilenko, A. K. Sheinkman, Chem. Heterocycl. Compd. (Engl. Transl.) 1988, 582;
67. g) R. Lavilla, T. Gotsens, M. Guerrero, C. Masdeu, M. C. Santano, C. Minguillón, J. Bosch, Tetrahedron 1997, 53, 13959;
68. h) J. L. Díaz, M. Miguel, R. Lavilla, J. Org. Chem. 2004, 69, 3550;
69. i) M. A. A. Meziane, J. P. Bazureau, Molecules 2002, 7, 252.
70. See also: j) W. Benson, E. Winterfeldt, Chem. Ber. 1979, 112, 1913;
71. k) A. I. Mayers, D. B. Miller, F. H. White, J. Am. Chem. Soc. 1988, 110, 4778.
72. R. M. Wilson, F. DiNinno, Jr., Tetrahedron Lett. 1970, 289.
73. 1H NMR spectroscopy.
74. 2 were obtained (95% conversion, d.r. = 7:1 and 80% ee at 0°C); MeCN also led to reasonable results (94 % conversion, d.r. = 6:1 and 77% ee at -20°C).
75. Compounds 7c and 7g were slightly unstable, which can account for the lower yield of isolation of these compounds.
76. The Cambridge Crystallographic Data Centre (CCDC) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the CCDC via www.ccdc.cam.ac.uk/data_request/cif.
77. For cation-π interactions in related systems, see, for example: a) S. Yamada, C. Morita, J. Am. Chem. Soc. 2002, 124, 8184;
78. b) T. Kawabata, M. Nagato, K. Takasu, K. Fuji, J. Am. Chem. Soc. 1997, 119, 3169;
79. c) D. L. Comins, S. P. Joseph, R. R. Goehring, J. Am. Chem. Soc. 1994, 116, 4719;
80. for reviews on cation-π or π-π interactions, see: d) J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303;
81. e) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651.