Sulfur ylide promoted synthesis of N-protected aziridines: A combined experimental and computational approach

Chemistry - A European Journal

Volumn 16, Issue 38, 2010, Pages 11744-11752

  Dokli, Irena ^a   Matanović, Ivana ^a   Hameršak, Zdenko ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Asymmetric synthesis; Azomethine ylides; Density functional calculations; Diastereoselectivity; Ylides

Indexed keywords

ASYMMETRIC SYNTHESIS; AZOMETHINE YLIDES; DENSITY FUNCTIONAL CALCULATIONS; DIASTEREOSELECTIVITY; YLIDES;

ISOMERS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; STEREOSELECTIVITY; SULFUR;

SYNTHESIS (CHEMICAL);

EID: 77957555439     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001436     Document Type: Article

References (63)

1. For reviews on asymmetric aziridinations and ring transformations, see: a) T. Tanner, Angew. Chem. 1994, 106, 625-646;
2. Angew. Chem. Int. Ed. Engl. 1994, 33, 599-619;
3. W. McCoull, F. A. Davis, Synthesis 2000, 1347-1365;
4. B. Zwanenburg, P. T. Holte, Top. Curr. Chem. 2001, 216, 93-124;
5. J. B. Sweeney, Chem. Soc. Rev. 2002, 31, 247-258;
6. e) P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905-2919;
7. Aziridines and Epoxides in Organic Synthesis (Ed.: A. K. Yudin), Wiley-VCH, Weinheim, 2006;
8. E. M. McGarrigle, E. L. Myers, O. Illa, M. A. Shaw, S. L. Riches, V. K. Aggarwal, Chem. Rev. 2007, 107, 5841-5883;
9. E. M. McGarrigle, V. K. Aggarwal in Enantioselective Organocatalysis: Reactions and Experimental Procedures (Ed.: P. I. Dalko), Wiley-VCH, Weinheim, 2007, Chapter 10;
10. G. K. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541-2569;
11. A. Padwa in Comprehensive Heterocyclic Chemistry III, Vol. 1 (Eds.: K. A. Katrizky, C. A. Ramsden, E. F V. Scriven, R. J. K. Taylor), Elsevier, Oxford, 2008, Chapter 1, p. 1;
12. H. Pellissier, Tetrahedron 2010, 66, 1509-1555.
13. a) K. B. Hansen, N. S. Finney, E. N. Jacobsen, Angew. Chem. 1995, 107, 750-752;
14. Angew. Chem. Int. Ed. Engl. 1995, 34, 676-678;
15. K. G. Rasmussen, K. A. Jorgensen, J. Chem. Soc. Perkin Trans. 1 1997, 1287-1292;
16. K. Juhl, R. G. Hazell, K. A. Jorgensen, J. Chem. Soc. Perkin Trans. 1 1999, 2293-2297;
17. J. C. Antilla, W. D. Wulff, J. Am. Chem. Soc. 1999, 121, 5099-5100;
18. e) J. C. Antilla, W. D. Wulff, Angew. Chem. 2000, 112, 4692;
19. Angew. Chem. Int. Ed. 2000, 39, 4518.
20. a) V. K. Aggarwal, A. Thompson, R. V. H. Jones, M. C. H. Standen, J. Org. Chem. 1996, 61, 8368-8369;
21. V. K. Aggarwal, E. Alonso, G. Fang, M. Ferrara, G. Hynd, M. Porcelloni, Angew. Chem. 2001, 113, 1482-1485;
22. Angew. Chem. Int. Ed. 2001, 40, 1433-1436;
23. V. K. Aggarwal, M. Ferrara, C. J. O'Brien, A. Thompson, R. V. H. Jones, R. Fieldhouse, J. Chem. Soc. Perkin Trans. 1 2001, 1635-1643;
24. V. K. Aggarwal, J. P. H. Charment, C. Ciampi, J. M. Hornby, C. J. O'Brien, G. Hynd, R. Parsons, J. Chem. Soc. Perkin Trans. 1 2001, 3159-3166;
25. e) V. K. Aggarwal, G. Hynd, W. Picoul, J.-L. Vasse, J. Am. Chem. Soc. 2002, 124, 9964-9965;
26. A. H. Li, Y. G. Zhou, L. X. Dai, X. L. Hou, L. J. Xia, J. Lin, J. Org. Chem. 1998, 63, 4338-4348;
27. X. L. Hou, J. Wu, R. H. Fan, C. H. Ding, Z. B. Luo, L. W. Dai, Synlett 2006, 181-193;
28. T. Saito, M. Sakairi, D. Akiba, Tetrahedron Lett. 2001, 42, 5451-5454;
29. D. Morton, D. Pearson, R. A. Field, R. A. Stockman, Org. Lett. 2004, 6, 2377-2380.
30. E. L. Eliel, J. E. Lynch, F. Kume, S. V. Frye, Org. Synth. 1987, 65, 214-223.
31. a) A. Solladié-Cavallo, A. Adib, Tetrahedron 1992, 48, 2453-2464;
32. A. Solladié-Cavallo, A. Diep-Vohuule, J. Org. Chem. 1995, 60, 3494-3498;
33. A. Solladié-Cavallo, A. Diep-Vohuule, V. Šunjić, V. Vinković, Tetrahedron: Asymmetry 1996, 7, 1783-1788;
34. A. Solladié-Cavallo, A. Diep-Vohuule, T. Isarno, Angew. Chem. 1998, 110, 1824-1827;
35. Angew. Chem. Int. Ed. 1998, 37, 1689-1691;
36. e) A. Solladié-Cavallo, M. Roje, T. Isarno, V. Šunjić, V. Vinković, Eur. J. Org. Chem. 2000, 1077-1080.
37. A. Solladié-Cavallo, M. Roje, R. Welter, V. Šunjić, J. Org. Chem. 2004, 69, 1409-1412.
38. I. Stipetić, M. Roje, Z. Hameršak, Synlett 2008, 3149-3152.
39. E. Vedejs, D. A. Engler, M. J. Mullins, J. Org. Chem. 1977, 42, 3109-3113.
40. A. Solladié-Cavallo, A. Adib, M. Schmitt, J. Fischer, A. De Cian, Tetrahedron: Asymmetry 1992, 3, 1597-1602.
41. N-SES imines and N-Ts imines were prepared according to: a) W. R. McKay, G. R. Proctor, J. Chem. Soc. Perkin Trans. 1 1981, 2435-2442;
42. W. B. Jennings, C. J. Lovely, Tetrahedron 1991, 47, 5561-5568.
43. N-Boc imines were prepared according to: c) A. M. Kanazawa, J. Denis, A. E. Greene, J. Org. Chem. 1994, 59, 1238-1240;
44. B. M. Trost, J. Jaratjaroonphong, V. Reutrakul, J. Am. Chem. Soc. 2006, 128, 2778-2779.
45. a) T. Hayashi, M. Ishigedani, J. Am. Chem. Soc. 2000, 122, 976-977;
46. Y. Xu, G. Lu, S. Matsunaga, M. Shibasaki, Angew. Chem. 2009, 121, 3403-3406;
47. Angew. Chem. Int. Ed. 2009, 48, 3353-3356.
48. a) R. Robiette, J. Org. Chem. 2006, 71, 2726-2734;
49. D. Janardanan, R. B. Sunoj, Chem. Eur. J. 2007, 13, 4805-4815;
50. D. Janardanan, R. B. Sunoj, J. Org. Chem. 2008, 73, 8163-8174;
51. Y. Arroyo, Á. Meana, J. F. Rodríguez, M. A. Sanz-Tejedor, I. Alonso, J. L. García Ruano, J. Org. Chem. 2009, 74, 4217-4224.
52. D. K. Wang, L. X. Dai, X. L. Hou, J. Chem. Soc. Chem. Commun. 1997, 1231-1232.
53. In fact there are two possible cisoid approaches, corresponding to S-C-C-N dihedral angle of approximately +60° or-60°. The geometries in Figure 2. correspond to the more stable conformation.
54. V. K. Aggarwal, J. N. Harvey, J. Richardson, J. Am. Chem. Soc. 2002, 124, 5747-5756.
55. G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449.
56. D. Janardanan, R. B. Sunoj, J. Org. Chem. 2007, 72, 331-341.
57. a) A. D. Becke, J. Chem. Phys. 1993, 98, 5684-5684;
58. A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100;
59. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789;
60. S. H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200-1211;
61. e) P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.
62. Gaussian 03, Revision B.05, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh, 2003.
63. 3).