Enantioselective desymmetrization of meso-N-(heteroarenesulfonyl)aziridines with TMSN3 catalyzed by chiral Lewis acids

Tetrahedron Letters

Volumn 51, Issue 29, 2010, Pages 3820-3823

  Nakamura, Shuichi ^a   Hayashi, Masashi ^a   Kamada, Yasutoshi ^a   Sasaki, Ryosuke ^a   Hiramatsu, Yuichi ^a   Shibata, Norio ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric catalysis; Chiral diamines; Chiral Lewis acids; Heteroarenesulfonyl groups; Stereocontroller

Indexed keywords

3,4 DICHLORO N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZENEACETAMIDE; AZIRIDINE DERIVATIVE; LEWIS ACID;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; PRECURSOR; RING OPENING; SYNTHESIS;

EID: 77954309282     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.065     Document Type: Article

References (59)

1. (a)Andrews, P.; Thomas, H.; Pohlke, R.; Seubert, J. Med. Res. Rev. 1983, 3, 147-200;
2. (b)Fenwick, A.; Keiser, J.; Utzinger, J. Drugs Future 2006, 31, 413-425.
3. Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669-1730.
4. (a)Szmuszkovicz, J.; Von Voigtlander, P. F. J. Med. Chem. 1982, 25, 1125-1126;
5. (b)Clark, C. R.; Halfpenny, P. R.; Hill, R. G.; Horwell, D. C.; Hughes, J.; Jarvis, T. C.; Rees, D. C.; Schofield, D. J. Med. Chem. 1988, 31, 831-836;
6. (c)Costello, G. F.; James, R.; Shaw, J. S.; Slater, A. M.; Stutchbury, N. C. J. J. Med. Chem. 1991, 34, 181-189;
7. (d)Barlow, J. J.; Blackburn, T. P.; Costello, G. F.; James, R.; Le Count, D. J.; Main, B. G.; Pearce, R. J.; Russell, K.; Shaw, J. S. J. Med. Chem. 1991, 34, 3149-3158
8. For biologically active chiral vicinal diamines, see: Kotti, S. R. S. S.; Timmons, C.; Li, G. Chem. Biol. Drug Des. 2006, 67, 101-114.
9. (a)For reviews, see: Lucet, D.; Gall, T. L.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627;
10. (b)Kizirian, J.-C. Chem. Rev. 2008, 108, 140-205.
11. (a)For reviews, see: Pineschi, M. Eur. J. Org. Chem. 2006, 4979-4988;
12. (b)Hu, X. E. Tetrahedron 2004, 60, 2701-2743;
13. (c)Schneider, C. Angew. Chem., Int. Ed. 2009, 48, 2082-2084.
14. (a)Li, Z.; Fernandez, M.; Jacobsen, E. N. Org. Lett. 1999, 1, 1611-1613;
15. (b)Furuta, Y.; Mita, T.; Fukada, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312-6313;
16. (c)Rowland, E. B.; Rowland, G. B.; Rivera-Otero, E.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 12084-12085;
17. (d)Wu, B.; Gallucci, J. C.; Parquette, J. R.; RajanBabu, T. V. Angew. Chem., Int. Ed. 2008, 47, 1126-1129;
18. (e)Wu, B.; Parquette, J. R.; RajanBabu, T. V. Science 2009, 326, 1662-1663.
19. (a)Nakamura, S.; Sato, N.; Sugimoto, M.; Toru, T. Tetrahedron: Asymmetry 2004, 15, 1513-1516;
20. (b)Sugimoto, H.; Nakamura, S.; Hattori, M.; Ozeki, S.; Shibata, N.; Toru, T. Tetrahedron Lett. 2005, 46, 8941-8944;
21. (c)Nakamura, S.; Nakashima, H.; Sugimoto, H.; Shibata, N.; Toru, T. Tetrahedron Lett. 2006, 47, 7599-7602;
22. (d)Nakamura, S.; Sano, H.; Nakashima, H.; Kubo, K.; Shibata, N.; Toru, T. Tetrahedron Lett. 2007, 48, 5565-5568;
23. (e)Nakamura, S.; Nakashima, H.; Sugimoto, H.; Sano, H.; Hattori, M.; Shibata, N.; Toru, T. Chem. Eur. J. 2008, 14, 2145-2152;
24. (f)Nakamura, S.; Nakashima, H.; Yamamura, A.; Shibata, N.; Toru, T. Adv. Synth. Catal. 2008, 350, 1209-1212;
25. Nakamura, S.; Sakurai, Y.; Nakashima, H.; Shibata, N.; Toru, T. Synlett 2009, 1639-1642;
26. (g)For enantioselective reaction using organocatalysts having a heteroarenesulfonyl group, see: Nakamura, S.; Hara, N.; Nakashima, H.; Kubo, K.; Shibata, N.; Toru, T. Chem. Eur.J. 2008, 14, 8079-8081;
27. (h)Hara, N.; Nakamura, S.; Shibata, N.; Toru, T. Chem. Eur. J. 2009, 15, 6790-6793.
28. (a)Enantioselective conjugate addition: Esquivias, J.; Arrayás, R. G.; Carretero, J. C. J. Org. Chem. 2005, 70, 7451-7454;
29. (b)Aza Diels-Alder reaction: Esquivias, J.; Arrayás, R. G.; Carretero, J. C. J. Am. Chem. Soc. 2007, 129, 1480-1481;
30. Esquivias, J.; Alonso, I.; Arrayás, R. G.; Carretero, J. C. Synthesis 2009, 113-126;
31. (d)Mannich-type reaction: González, A. S.; Arrayás, R. G.; Carretero, J. C. Org. Lett. 2006, 8, 2977-2980;
32. (e)Hernández-Toribio, J.; Arrayás, R. G.; Carretero, J. C.J. Am. Chem. Soc. 2008, 130, 16150-16151;
33. (f)Hernández-Toribio, J.; Arrayás, R. G.; Carretero, J. C. Chem. Eur. J. 2010, 16, 1153-1157;
34. (g)Morimoto, H.; Lu, G.; Aoyama, N.; Matsunaga, S.; Shibasaki, M.J. Am. Chem. Soc. 2007, 129, 9588-9589;
35. (h)Lu, G.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2008, 47, 6847-6850;
36. (i)González, A. S.; Arrayás, R. G.; Rivero, M. R.; Carretero, J. C. Org. Lett. 2008, 10, 4335-4337.
37. (a)N-(Heteroarenesulfonyl)aziridines were prepared by reported procedures, see: Wright, S. W.; Hallstrom, K. N.J. Org. Chem. 2006, 71, 1080-1084;
38. (b)Mordini, A.; Russo, F.; Valacchi, M.; Zani, L.; Degl'Innocenti, A; Reginato, G. Tetrahedron 2002, 58, 7153-7163
39. 2)2/3
40. 3
41. (a)Szmuszkovicz, J. Prog. Drug Res. 1999, 53,1-51;
42. (b)Bachand, B.; Tarazi, M.; St-Denis, Y.; Edmunds, J. J.; Winocour, P. D.; Leblond, L; Siddiqui, M. A. Bioorg. Med. Chem. Lett. 2001, 11, 287-290;
43. (c)St-Denis, Y.; Levesque, S.; Bachand, B.; Edmunds, J. J.; Leblond, L.; Preville, P.; Tarazi, M.; Winocour, P. D.; Siddiqui, M. A. Bioorg. Med. Chem. Lett. 2002, 12,1181-1184;
44. (d)Bursavich, M. G.; Rich, D. H. J. Med. Chem. 2002, 45, 541-558
45. (a)De Costa, B. R.; Bowen, W. D.; Hellewell, S. B.; George, C; Rothman, R. B.; Reid, A. A.; Walker, J. M.; Jacobson, A. E.; Rice, K. C. J. Med. Chem. 1989, 32, 1996-2002;
46. (b)De Costa, B. R.; Bowen, W. D.; Thurkauf, A; Finn, D. T.; Vazirani, S.; Rothman, R. B.; Band, L; Contreras, P. C; Gray, N. M.J. Med. Chem. 1990,33, 3100-3110
47. (a)Previously, (1S,2S)-U-50,488 was synthesized through an enzymatic resolution, see: González-Sabín, J.; Gotor, V.; Rebolledo, F. Chem. Eur. J. 2004, 10, 5788-5794
48. (b)For dynamic kinetic resolution using ruthenium-catalyzed hydrogenation, see: Liu, S.; Xie, J.-H.; Wang, L-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2007, 46, 7506-7508.
49. S 19.1 (major) min.
50. -1; MS(ESI) m/z 270.1 [M+H].
51. S 16.3 (major) min.
52. R 6.0 (minor) min.
53. 3), 1.55-1.85 (m, 8H), 2.30-1.70 (m, 5H), 3.20-3.40 (m, 1H, CH), 5.25 (br, 1H, NH); MS(ESI) m/z 269.3 [M+H]. 17.
54. (a)Goulaouic-Dubois, C; Guggisberg, A.; Hesse, M. J. Org. Chem. 1995, 60, 5969-5972;
55. (b)Pak, C. S.; Lim, D. S. Synth. Commun. 2001, 31, 2209-2214
56. (a)A tetrahedral Mg(II) complex has been proposed, see: Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810;
57. Sibi, M. P.; Sausker, J. B. J. Am. Chem. Soc. 2002, 124, 984-991;
58. (b)An octahedral structure has been also proposed: Sibi, M. P.; Petrovic, G.; Zimmerman, J. J. Am. Chem. Soc. 2005, 127, 2390-2391;
59. (d)Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488.