Enantioselective addition of nitrones to activated cyclopropanes

Journal of the American Chemical Society

Volumn 127, Issue 16, 2005, Pages 5764-5765

  Sibi, Mukund P ^a   Ma, Zhihua ^a   Jasperse, Craig P ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; NICKEL COMPLEX; NITRONE; NITRONE DERIVATIVE; OXAZINE DERIVATIVE; OXAZOLE DERIVATIVE; TETRAHYDRO 1,2 OXAZINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY;

CYCLOPROPANES; NITROGEN OXIDES; OXAZINES; STEREOISOMERISM;

EID: 17744393466     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0421497     Document Type: Article

References (28)

1. (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66.
2. (b) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
3. (c) Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321.
4. (a) Beal, R. B.; Dombrowski, M. A.; Snider, B. B. J. Org. Chem. 1986, 51, 4391.
5. (b) Kotsuki, H.; Arimura, K.; Maruzawa, R.; Ohshima, R. Synlett 1999, 650.
6. (c) England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. A. J. Org. Chem. 2001, 66, 4704.
7. (a) Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023.
8. (b) Young, I. S.; Kerr, M. A. Org. Lett. 2004, 6, 139.
9. Ganton, M. D.; Kerr, M. A. J. Org. Chem. 2004, 69, 8554. For recent work on donor-acceptor cyclopropanes, see: Yu, M.; Pagenkopf, B. L. J. Am. Chem. Soc. 2003, 125, 8122.
10. Ganton, M. D.; Kerr, M. A. J. Org. Chem. 2004, 69, 8554. For recent work on donor-acceptor cyclopropanes, see: Yu, M.; Pagenkopf, B. L. J. Am. Chem. Soc. 2003, 125, 8122.
11. Approaches to tetrahydro-1,2-oxazines: (a) Pulz, R.; Cicchi, S.; Brandi, A. Reissig, H.-U. Eur. J. Org. Chem. 2003, 1153. (b) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962. (c) Yoon, S. C.; Kim, K.; Park, Y. J. J. Org. Chem. 2001, 66, 7334.
12. Approaches to tetrahydro-1,2-oxazines: (a) Pulz, R.; Cicchi, S.; Brandi, A. Reissig, H.-U. Eur. J. Org. Chem. 2003, 1153. (b) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962. (c) Yoon, S. C.; Kim, K.; Park, Y. J. J. Org. Chem. 2001, 66, 7334.
13. Approaches to tetrahydro-1,2-oxazines: (a) Pulz, R.; Cicchi, S.; Brandi, A. Reissig, H.-U. Eur. J. Org. Chem. 2003, 1153. (b) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962. (c) Yoon, S. C.; Kim, K.; Park, Y. J. J. Org. Chem. 2001, 66, 7334.
14. Yu, Q.-s.; Zhu, X.; Holloway, H. W.; Whittaker, N. F.; Brossi, A.; Greig, N. H. J. Med. Chem. 2002, 45, 3684-3691.
15. (a) Pulz, R.; Al-Harrasi, A.; Reissig, H.-U. Org. Lett. 2002, 4, 2353.
16. (b) Buchholz, M.; Reissig, H.-U. Eur. J. Org. Chem. 2003, 3524.
17. (c) Tishkov, A. A.; Reissig, H.-U.; Ioffe, S. L. Synlett 2002, 863.
18. (a) Uchida, I.; Shigehiro, T.; Hiroshi, K.; Sumio, K.; Hashimoto, M.; Tada, T.; Shigetaka, K.; Morimoto, Y. J. Am. Chem. Soc. 1987, 109, 4108.
19. (b) Terano, H.; Takase, S.; Hosoda, J.; Kohsaka, M. J. Antibiot. 1989, 42, 145.
20. For enantioselective reactions involving nitrones, see: (a) Carmona, D.; Lamata, M. P.; Viguri, F.; Rodriguez, R.; Oro, L. A.; Balana, A. I.; Lahoz, F. J.; Tejero, T.; Merino, P.; Franco, S.; Montesa, I. J. Am. Chem. Soc. 2004, 126, 2716-2717. (b) Sibi, M. P.; Ma, Z.; Jasperse, C. P. J. Am. Chem. Soc. 2004, 126, 718-719.
21. For enantioselective reactions involving nitrones, see: (a) Carmona, D.; Lamata, M. P.; Viguri, F.; Rodriguez, R.; Oro, L. A.; Balana, A. I.; Lahoz, F. J.; Tejero, T.; Merino, P.; Franco, S.; Montesa, I. J. Am. Chem. Soc. 2004, 126, 2716-2717. (b) Sibi, M. P.; Ma, Z.; Jasperse, C. P. J. Am. Chem. Soc. 2004, 126, 718-719.
22. For reaction conditions and other experimental details, see Supporting Information.
23. (a) Kanemasa, S.; Oderaotoshi, Y.; Tanaka, J.; Wada, E. J. Am. Chem. Soc. 1998, 120, 12355.
24. (b) Shirahase, M.; Kanemasa, S.; Oderaotoshi, Y. Org. Lett. 2004, 6, 675.
25. (c) Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074.
26. 2-4g.
27. 2-4g, no enantiomeric enrichment was observed. This suggests that nitrone addition is irreversible with stereoselectivity under kinetic control.
28. Nonselective C-O bond formation probably occurs first, remote from and uncontrolled by the chiral nickel malonate, followed by nickel-controlled formation of C3. An alternative possibility is that C-C bond formation may occur first, but neither the nickel nor C3 stereocenters provide high stereoinduction at the C-O bond forming step.