Asymmetric catalytic aziridination of dihydronaphthalenes for the preparation of substituted 2-aminotetralins

Tetrahedron

Volumn 66, Issue 52, 2010, Pages 9790-9797

  Aaseng, Jon Erik ^a   Melnes, Silje ^a   Reian, Gard ^a   Gautun, Odd R ^a  

^a NORWEGIAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Norway)

Author keywords

2 Aminotetralins; Catalytic asymmetric aziridination; Catalytic racemic aziridination; Dihydronaphthalenes; N (p Toluenesulfonyl)iminophenyliodinane

Indexed keywords

1,2,3,4 TETRAHYDRO 2 NAPHTHALENAMINE; 1,2,3,4 TETRAHYDRO 7 METHOXY 2 NAPHTHALENAMINE; 2 (4 METHYLBENZENESULFONYL)AMINO 1,2,3,4 TETRAHYDRONAPHTHALENE; 2 (4 METHYLBENZENESULFONYL)AMINO 6 ACETOXY 1,2,3,4 TETRAHYDRONAPHTHALENE; 2 (4 METHYLBENZENESULFONYL)AMINO 7 METHOXY 1,2,3,4 TETRAHYDRONAPHTHALENE; 2 AMINO 7 METHOXYTETRALIN; 2 AMINOTETRALIN; 2 AMINOTETRALIN DERIVATIVE; 2 TRIFLUOROACETYLAMINO 1,2,3,4 TETRAHYDRONAPHTHALENE; 6 ACETOXY 3,4 DIHYDRONAPHTHALENE; 7 METHOXY 2 (TRIFLUOROACETYLAMINO) 1,2,3,4 TETRAHYDRONAPHTHALENE; AZIRIDINE DERIVATIVE; BENZYL DERIVATIVE; COPPER; N (4 METHOXYBENZENESULFONYL)AMINO 1,2,3,4 TETRAHYDRONAPHTHALENE 1,2 IMINE; N (4 METHYLBENZENESULFONYL)AMINO 1,2,3,4 TETRAHYDRO 6 ACETOXYNAPHTHALENE 1,2 IMINE; N (4 METHYLBENZENESULFONYL)AMINO 1,2,3,4 TETRAHYDRO 7 METHOXYNAPHTHALENE 1,2 IMINE; N (4 METHYLBENZENESULFONYL)AMINO 1,2,3,4 TETRAHYDRONAPHTHALENE 1,2 IMINE; N (4 NITROBENZENESULFONYL)AMINO 1,2,3,4 TETRAHYDRO 6 ACETOXYNAPHTHALENE 1,2 IMINE; N (4 NITROBENZENESULFONYL)AMINO 1,2,3,4 TETRAHYDRO 7 METHOXYNAPHTHALENE 1,2 IMINE; N (4 NITROBENZENESULFONYL)AMINO 1,2,3,4 TETRAHYDRONAPHTHALENE 1,2 IMINE; NAPHTHALENE DERIVATIVE; NITROGEN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; AZIRIDINATION; CHEMICAL MODIFICATION; DEPROTECTION REACTION; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENOLYSIS; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; STEREOCHEMISTRY;

EID: 78649668777     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.11.010     Document Type: Article

References (82)

1. E. Bamberger, and W. Filehne Ber. Dtsch. Chem. Ges. 22 1889 777 778
2. ® search of '2-aminotetralin' and '2-aminotetralins' resulted in a more than 700 hits, a great part of them concerning studies of physiological properties of 2-aminotetralin derivatives (08.02.2010).
3. For selected reviews covering dopamine and serotonin receptor ligands with antagonist properties, see:
4. A.E. Hackling, and H. Stark ChemBioChem 3 2002 946 961
5. M.L. Carlsson, A. Carlsson, and M. Nilsson Curr. Med. Chem. 11 2004 267 277
6. G. Caliendo, V. Santagada, E. Perissutti, and F. Fiorino Curr. Med. Chem. 12 2005 1721 1753
7. H.-J. Federsel, M. Hedberg, F.R. Qvarnström, M.P.T. Sjögren, and W. Tian Acc. Chem. Res. 40 2007 1377 1384
8. V. Ruggiero, P. Piovesan, C. Fabrizi, G.M. Lauro, S. Campo, C. Albertoni, E. Nucera, P. Carminati, and O. Ghirardi Shock 21 2004 77 85
9. Fanto N.; Moretti, G.P.; Foresta, P. WO 9,915,494 A1, 1999;
10. Chem. Abstr. 130 1999 237373
11. Morreti, G.P.; Foresta, P. WO 9,833,762 A1, 1998;
12. Chem. Abstr. 129 1998 161424
13. For examples of resolution of precursors for the synthesis of optical active 2-aminotetralins, see:
14. B.A. Hathaway, D.E. Nichols, M.B. Nichols, and G.K.W. Yim J. Med. Chem. 25 1982 535 538
15. Cecchi, R.; Barzaghi, L.; Guzzi, U. EP 678,579 A1, 1995;
16. Chem. Abstr. 124 1995 28113
17. T. Yanagi, K. Kikuchi, H. Takeuchi, T. Ishikawa, T. Nishimura, T. Kamijo, and I. Yamamoto Chem. Pharm. Bull. 2001 340 344
18. P. Bonomi, P. Cairoli, D. Ubiali, C.F. Morelli, M. Filice, I. Nieto, M. Pregnolato, P. Manitto, M. Terreni, and G. Speranza Tetrahedron: Asymmetry 20 2009 467 472
19. F. Orsini, G. Sello, E. Travaini, and P. Di Gennaro Tetrahedron: Asymmetry 13 2002 253 259
20. For selected examples of optical resolution of racemic 2-aminotetralins, see:
21. Arvidsson, F.L.-E.; Carlsson, P.A.E.; Hacksell, U.A.; Hjorth, J.S.M.; Johansson, A.M.; Lindberg, P.L.; Nilsson, J.L.G.; Sanchez, D.; Wikström, H.V. WO 8,204,042 A1, 1982;
22. Chem. Abstr. 99 1983 5381
23. A.M. Johansson, J.L.G. Nilsson, A. Karlén, U. Hacksell, D. Sanchez, K. Svensson, S. Hjorth, A. Carlsson, S. Sundell, and L. Kenne J. Med. Chem. 30 1987 1827 1837
24. A. Karlsson, C. Pettersson, S. Sundell, L.-E. Arvidsson, and U. Hacksell Acta Chem. Scand. B 42 1988 231 236
25. Andersson, B.R.; Carlsson, P.A.E.; Svensson, K.A.I.; Wikstrom, H.V. EP 334,538 A1, 1989;
26. Chem. Abstr. 113 1990 152060
27. Lin, C.-H.; Haadsna, S.R.; Piercey, M.F.; Romero, A.G.; Darlington, W.H. WO 9,206,967, 1992;
28. Chem. Abstr. 117 1992 251360
29. Z.-P. Zhuang, M.-P. Kung, W. Clarke, S. Maayani, M. Mu, and H.F. Kung Chirality 7 1995 452 458
30. C. Sonesson, T. Barf, J. Nilsson, D. Dijkstra, A. Carlsson, K. Svensson, M.W. Smith, I.J. Martin, J.N. Duncan, L.J. King, and H. Wikström J. Med. Chem. 38 1995 1319 1329
31. Yamaura, M. JP 2,002,275,131 A, 2002;
32. Chem. Abstr. 137 2002 247515
33. Amari, G.; Del Canale, M.; Razzetti, R.; Monici Pret, P.A.; Rondelli, I. WO 200,185,668 A1, 2001
34. Chem. Abstr. 135 2001 357780
35. For selected examples applying L-aspartic acid and derivatives as chiral pool in the synthesis of enantiomeric pure 2-aminotetralins, see:
36. F. Zymalkowski, and E. Dornhege Tetrahedron Lett. 9 1968 5743 5746
37. F. Zymalkowski, and E. Dornhege Liebigs Ann. Chem. 728 1969 144 151
38. J.E. Norlander, M.J. Payne, F.G. Njoroge, V.M. Vishwanath, G.R. Han, G.D. Laikos, and M.A. Balk J. Org. Chem. 50 1985 3619 3622
39. R. Cecchi, T. Croci, R. Boigegrain, S. Boveri, M. Baroni, G. Boccardi, J.P. Guimbard, and U. Guzzi Eur. J. Med. Chem. 29 1994 259 267
40. Aaseng, J.E.; Gautun, O.R. Tetrahedron 2010, 66, 8982-8991.
41. B. Quiclet-Sire, G. Revol, and S.Z. Zard Org. Lett. 11 2009 3554 3557
42. Honda, T.; Fujii, A.; Inoue, K.; Yasohara, Y.; Itagaki, Y.; Mahehara, K.; Takeda, T.; Ueda, Y. WO 2,003,046,197 A1, 2003;
43. Chem. Abstr. 139 2003 5760
44. A.R. Martin, R. DiSanto, I. Plotnikov, S. Kamat, D. Shonnard, and S. Pannuri Biochem. Eng. J. 37 2007 246 255
45. P.J. Murray, R.M. Helden, M.R. Johnson, G.M. Robertson, D.I.C. Scopes, M. Stokes, S. Wadman, J.W.F. Whitehead, A.G. Hayes, G.J. Kilpatric, C. Large, C.M. Stubbs, and M.P. Turpin Bioorg. Med. Chem. Lett. 6 1996 403 408
46. H.-J. Federsel, M. Hedberg, F.R. Qvarnström, and W. Tian Org. Process Res. Dev. 12 2008 512 521
47. For selected examples of asymmetric catalytic hydrogenation of prochiral and cyclic ene carbamates, see:
48. Z. Zhang, G. Zhu, Q. Jiang, D. Xiao, and X. Zhang J. Org. Chem. 64 1999 1774 1775
49. M. Devocelle, A. Mortreux, F. Agbossou, and J.-R. Dormoy Tetrahedron Lett. 40 1999 4551 4554
50. P. Dupau, A.-E. Hay, C. Bruneau, and P.H. Dixneuf Tetrahedron: Asymmetry 12 2001 863 867
51. Burk, M.J.; Malan, C.G. WO 2,001,094,359 A1, 2001;
52. Chem. Abstr. 136 2001 37771
53. J.L. Renaud, P. Dupau, A.-E. Hay, M. Guingouain, P.H. Dixneuf, and C. Bruneau Adv. Synth. Catal. 345 2003 230 238
54. X.-B. Jiang, L. Lefort, P.E. Goudriaan, A.H.M. de Vries, P.W.N.M. van Leeuwen, J.G. de Vries, and J.N.H. Reek Angew. Chem., Int. Ed. 45 2006 1223 1227
55. A.J. Sandee, A.M. van der Burg, and J.N.H. Reek Chem. Commun. 2007 864 866
56. X. Sala, I. Serrano, M. Rodríguez, I. Romero, A. Llobet, and P.W.N.M. van Leeuwen Catal. Commun. 9 2007 117 119
57. M. Imanishi, Y. Nakajima, Y. Tomishima, H. Hamashima, K. Washizuka, M. Sakurai, S. Matsui, E. Imamura, K. Ueshima, T. Yamamoto, N. Yamamoto, H. Ishikawa, K. Nakano, N. Unami, K. Hamada, Y. Matsumura, F. Takamura, and K. Hattori J. Med. Chem. 51 2008 4804 4822
58. F.W. Patureau, S. de Boer, M. Kuil, J. Meeuwissen, P.-A.R. Breuil, M.A. Siegler, A.L. Spek, A.J. Sandee, B. de Bruin, and J.N.H. Reek J. Am. Chem. Soc. 131 2009 6683 6685
59. J. Meeuwissen, M. Kuil, A.M. van der Burg, A.J. Sandee, and J.N.H. Reek Chem. - Eur. J. 15 2009 10272 10279
60. E.N. Jacobsen E.N. Jacobsen, A. Phaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis Vol. 2 1999 Springer Berlin 607 618 For selected reviews cowering azymmetric aziridination, see
61. P. Müller, and C. Fruit Chem. Rev. 103 2003 2905 2917
62. Pellissier Hélne Tetrahedron 66 2010 1509 1555
63. Z. Li, K.R. Conser, and E.N. Jacobsen J. Am. Chem. Soc. 115 1993 5326 5327
64. Z. Li, R.W. Quan, and E.N. Jacobsen J. Am. Chem. Soc. 117 1995 5889 5890
65. D.A. Evans, M.M. Faul, M.T. Bilodeau, B.A. Anderson, and D.M. Barnes J. Am. Chem. Soc. 115 1993 5328 5329
66. D.A. Evans, M.M. Faul, and M.T. Bilodeau J. Am. Chem. Soc. 116 1994 2742 2753
67. S. Hajra, B. Maji, and D. Mal Adv. Synth. Catal. 351 2009 859 864
68. F.M. Hauser, and S. Prasanna Synthesis 1980 621 623
69. Implementation of a successful procedure described for a steroid derivative with some similiraities to olefin 1d, see: J.J. Harburn, G.C. Loftus, and B.A. Marples Tetrahedron 54 1998 11907 11924
70. A.J. Catino, J.M. Nicholos, R.E. Forslund, and M.P. Doyle Org. Lett. 7 2005 2787 2790
71. P. Müller, C. Baud, and Y. Jacquier Tetrahedron 52 1996 1543 1548
72. P. Müller, C. Baud, and Y. Jacquier Can. J. Chem. 76 1998 738 750
73. C. Bolm, and O. Simić J. Am. Chem. Soc. 123 2001 3830 3831
74. D. Tanner, and O.R. Gautun Tetrahedron 51 1995 8279 8288
75. Z. Moussa, and D. Romo Synlett 2006 3294 3298
76. P. Brandt, M.J. Södergren, P.G. Andersson, and P.-O. Norrby J. Am. Chem. Soc. 122 2000 8013 8020
77. C. Bolchi, P. Catalano, L. Fumagalli, M. Gobbi, M. Pallavicini, A. Pedretti, L. Villa, G. Vistoli, and E. Valoti Bioorg. Med. Chem. 12 2004 4937 4951
78. E. Mosettig, and E.L. May J. Org. Chem. 5 1940 528 543
79. G.-Y. Gao, J.D. Harden, and X.P. Zhang Org. Lett. 7 2005 3191 3193
80. G.F. Keaney, and J.L. Wood Tetrahedron Lett. 46 2005 4031 4034
81. E. Gómez-Sánches, E. Soriano, and J. Marco-Contelles J. Org. Chem. 72 2007 8656 8670
82. Y. Qizhuang, and G.L. Grunewald J. Med. Chem. 32 1989 478 486