Highly diastereoselective alkylation of aziridine-2-carboxylate esters: Enantioselective synthesis of LFA-1 antagonist BIRT-377

Angewandte Chemie - International Edition

Volumn 44, Issue 38, 2005, Pages 6169-6172

  Patwardhan, Aniruddha P ^a   Pulgam, V Reddy ^a   Zhang, Yu ^a   Wulff, William D ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Aziridines; BIRT 377; Enols; Synthetic methods

Indexed keywords

ASYMMETRIC CATALYSIS; AZIRIDINES; BIRT-377; ENOLS; SYNTHETIC METHODS;

ALKYLATION; CATALYSIS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ESTERS;

AZIRIDINE 2 CARBOXYLIC ACID; AZIRIDINE DERIVATIVE; AZIRIDINE-2-CARBOXYLIC ACID; BIRT 377; ESTER; IMIDAZOLIDINE DERIVATIVE; LYMPHOCYTE FUNCTION ASSOCIATED ANTIGEN 1;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKYLATION; AZIRIDINES; ESTERS; IMIDAZOLIDINES; LYMPHOCYTE FUNCTION-ASSOCIATED ANTIGEN-1; MOLECULAR STRUCTURE;

EID: 25844477438     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500923     Document Type: Article

References (50)

1. P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905-2920.
2. a) J. C. Antilla, W. D. Wulff, J. Am. Chem. Soc. 1999, 121, 5099-5100;
3. b) J. C. Antilla, W. D. Wulff, Angew. Chem. 2000, 112, 4692-4695;
4. Angew. Chem. Int. Ed. 2000, 39, 4518-4521;
5. c) C. Loncaric, W. D. Wulff, Org. Lett. 2001, 3, 3675-3678;
6. d) J. Antilla, W. D. Wulff, Y. Zhang, unpublished results.
7. 4 at 85°C for 1 h and then by removing the volatiles under a high vacuum at 85°C for 30 minutes.
8. For other examples of aziridines from the reactions of imines with diazo compounds, see references [2a], [2b], and references therein, and the following: a) S. H. Lee, I. W. Song, Bull. Korean Chem. Soc. 2005, 26, 223-224;
9. b) M. Redlich, M. M. Hossain, Tetrahedron Lett. 2004, 45, 8987-8990;
10. c) B. Vanderhoydonck, C. V. Stevens, Synthesis 2004, 722-734;
11. d) A. L. Williams, J. N. Johnston, J. Am. Chem. Soc. 2004, 126, 1612-1613;
12. e) Y. Li, P. W. H. Chan, N.-Y. Zhu, C.-M. Che, H.-L. Kwong, Organometallics 2004, 23, 54-66;
13. f) J. R. Krumper, M. Gerisch, J. M. Suh, R. G. Bergman, T. D. Tilley, J. Org. Chem. 2003, 68, 9705-9710;
14. g) J. S. Yadav, B. V. S. Reddy, P. N. Reddy, M. S. Rao, Synthesis 2003, 1387-1390;
15. h) T. Akiyama, S. Ogi, K. Fuchibe, Tetrahedron Lett. 2003, 44, 4011-4013;
16. i) J. S. Yadav, B. V. S. Reddy, M. S. Rao, P. N. Reddy, Tetrahedron Lett. 2003, 44, 5275-5278;
17. j) W. Sun, C.-G. Zia, H.-W. Wang, Tetrahedron Lett. 2003, 44, 2409-2411;
18. k) E. Hevia, J. Perez, V. Riera, D. Miguel, S. Kassel, A. Rheingold, Inorg. Chem. 2002, 41, 4673-4679;
19. l) M. F. Mayer, M. M. Hossain, J. Organomet. Chem. 2002, 654, 202-209;
20. m) V. K. Aggarwal, E. Alonso, M. Ferrara, S. E. Spey, J. Org. Chem. 2002, 67, 2335-2344;
21. n) D. Morales, J. Perez, L. Riera, V. Riera, R. Corzo-Suarez, S. Garcia-Granda, D. Miguel, Organometallics 2002, 21, 1540-1545;
22. o) M. P. Spanedda, B. Crousse, S. Narizuka, D. Bonnet-Delphon, J.-P. Begue, Collect. Czech. Chem. Commun. 2002, 67, 1359-1365;
23. p) K.-D. Lee, J.-M Suh, J.-H. Park, H.-J. Ha, H. G. Choi, C. S. Park, J. W. Chang, W. K. Lee, Y. Dong, H. Yun, Tetrahedron 2001, 57, 8267-8276;
24. q) 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;
25. r) B. Crousse, S. Narizuka, D. Bonnet-Delpon, J.-P. Begue, Synlett 2001, 5, 679-681;
26. s) M. P. Doyle, W. Hu, D. J. Timmons, Org. Lett. 2001, 3, 933-935;
27. t) M. F. Mayer, Q. Wang, M. M. Hossain, J. Organomet. Chem. 2001, 630, 78-83;
28. u) V. K. Aggarwal, E. Alonso, G. Fang, M. Ferrara, G. Hynd, M. Porcelloni, Angew. Chem. 2001, 113, 1482-1485;
29. Angew. Chem. Int. Ed. 2001, 40, 1433-1436;
30. v) S. H. Lee, T. D. Han, K. Yu, K. H. Ahn, Bull. Korean Chem. Soc. 2001, 22, 449-450;
31. w) V. K. Aggarwal, M. Ferrara, Org. Lett. 2000, 2, 4107-4110;
32. x) R. Hori, T. Aoyama, T. Shioiri, Tetrahedron Lett. 2000, 41, 9455-9458;
33. y) S. Sengupta, S. Mondal, Tetrahedron Lett. 2000, 41, 6245;
34. z) T. Kubo, S. Sakaguchi, Y. Ishii, Chem. Commun. 2000, 625-626;
35. aa) W. Xie, J. Fang, J. Li, P. G. Wang, Tetrahedron 1999, 55, 12 929-12 938;
36. ab) D. L. Wright, M. C. McMills, Org. Lett. 1999, 1, 667-670;
37. ac) K. Juhl, R. G. Hazell, K. A. Jorgensen, J. Chem. Soc. Perkin Trans. 1 1999, 2293-2297.
38. a) C. Cativiela, M. D. Diaz-de-Villegas, Tetrahedron: Asymmetry 1998, 9, 3517-3599;
39. b) C. Cativiela, M. D. Diaz-de-Villegas, Tetrahedron: Asymmetry. 2000, 11, 645-732.
40. a) D. Seebach, R. Häner, Chem. Lett. 1987, 49-52;
41. b) R. Häner, B. Olano, D. Seebach, Helv. Chim. Acta 1987, 70, 1676-1691.
42. a) V. Alezra, M. Bonin, L. Micouin, H.-P. Husson, Tetrahedron Lett. 2000, 41, 651-654;
43. b) V. Alezra, M. Bonin, L. Micouin, C. Policar, H.-P. Husson, Eur. J. Org. Chem. 2001, 2589-2594.
44. a) N. K. Yee, Org. Lett. 2000, 2, 2781-2784;
45. b) E. Napolitano, V. Farina, Tetrahedron Lett. 2001, 42, 3231-3234;
46. c) R. P. Frutos, S. Stehle, L. Nummy, N. Yee, Tetrahedron: Asymmetry 2001, 12, 101-104;
47. d) S. R. Kapadia, D. M. Spero, M. Eriksson, J. Org. Chem. 2001, 66, 1903-1905;
48. e) N. S. Chowdari, C. F. Barbas III, Org. Lett. 2005, 7, 867-870.
49. a) E. Vedejs, A. Klapars, D. L. Warner, A. H. Weiss, J. Org. Chem. 2001, 66, 7542-7546;
50. b) B. Carboni, L. Monnier, Tetrahedron 1999, 55, 1197-1248.