Magnesium iodide promoted reactions of nitrones with cyclopropanes: A synthesis of tetrahydro-1,2-oxazines

Journal of Organic Chemistry

Volumn 69, Issue 24, 2004, Pages 8554-8557

  Ganton, Michael D ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; AMINES; CATALYSIS; ESTERS; KETONES; PARAFFINS; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

1,1-CYCLOPROPANE DIESTERS; CYCLOADDITION REACTIONS; CYCLOPROPANES; MAGNESIUM IODIDE;

MAGNESIUM COMPOUNDS;

ALDEHYDE; CYCLOPROPANE DERIVATIVE; ESTER DERIVATIVE; HYDROXYLAMINE; MAGNESIUM DERIVATIVE; MAGNESIUM IODIDE; NITRONE DERIVATIVE; OXAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CIS ISOMER; DIASTEREOISOMER; QUANTUM YIELD; STEREOCHEMISTRY; SYNTHESIS;

EID: 9344248075     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048768f     Document Type: Article

References (21)

1. (a) Uchida, I.; Shigehiro, T.; Hiroshi, K.; Sumio, K.; Hashimoto, M.; Tada, T.; Shigetaka, K.; Morimoto, Y. J. Am. Chem. Soc. 1987, 109, 4108-4109.
2. (b) Terano, H.; Takase, S.; Hosoda, J.; Kohsaka, M. J. Antibiot. 1989, 42, 145-148.
3. (a) Tsoungas, P. G. Heterocycles 2002, 57, 1149-1178.
4. (b) Gilchrist, T. L.; Wood, J. E. In Comprehensive Heterocyclic Chemistry II; Eisevier: Oxford, UK, 1996; Vol. 6, pp 279-299 and 1177-1307.
5. Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 26, 3023-3026.
6. Young, I. S.; Kerr, M. A. Org. Lett. 2004, 6, 139-141.
7. (a) Meyers, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 694-696.
8. (b) Lerchner, A.; Carreira, E. M. J. Am Chem. Soc. 2002, 124, 14826-14827.
9. (c) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175-1181.
10. (d) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186-3189.
11. (a) Lautens, M.; Han, W.; Liu, J. H.-C. J. Am. Chem. Soc. 2003, 125, 4028-4029.
12. (b) Lautens, M.; Han, W J. Am. Chem. Soc. 2002, 124, 6312-6316.
13. (a) Bertozzi, F.; Gundersen, B. V.; Gustafsson, M.; Olsson, R. Org. Lett. 2003, 5, 1551-1554.
14. (b) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147-3150.
15. For excellent reviews on activated cyclopropanes in synthesis see: (a) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196.
16. (b) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198.
17. (c) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66.
18. Gautheron-Chapoulaud, V.; Pandya, S. U.; Cividino, P.; Masson, G.; Py, S.; Vallee, Y. Synlett 2001, 1281-1283.
19. 7g: commercially available (Aldrich). 7d: Kierstead, R. W.; Linstead, R. P.; Weedon, B. C. L. J. Chem. Soc. 1952, 3610-3616. 7a-c,e,f: Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353-1364.
20. 7g: commercially available (Aldrich). 7d: Kierstead, R. W.; Linstead, R. P.; Weedon, B. C. L. J. Chem. Soc. 1952, 3610-3616. 7a-c,e,f: Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353-1364.
21. Anwander, R. In Lanthanides: Chemistry and Use in Organic Synthesis; Springer-Verlag: Berlin, Germany, 1999; p 23.