Examination of homo-[3 + 2]-dipolar cycloaddition: Mechanistic insight into regio-and diastereoselectivity

Journal of Organic Chemistry

Volumn 72, Issue 26, 2007, Pages 10251-10253

  Karadeolian, Avedis ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; CATALYST SELECTIVITY; CYCLOADDITION; REACTION RATES; SUBSTITUTION REACTIONS;

CYCLOPROPANEDIESTERS; CYCLOPROPANES; DIASTEREOSELECTIVITY; LEWIS ACIDS;

ESTERS;

CYCLOPROPANE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ISOMER; STEREOCHEMISTRY;

EID: 37549006038     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702073w     Document Type: Article

References (11)

1. Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023.
2. (a) Canton, M. D.; Kerr, M. A. J. Org. Chem. 2004, 69, 8554.
3. (b) Young, I. S.; Kerr, M. A. Org. Lett. 2004, 6, 139.
4. (a) Kang, Y.-B.; Sun, X.-L.; Tang, Y. Angew. Chem., Int. Ed. 2007, 46, 3918.
5. (b) Sibi, M. P.; Zhihua, M.; Jasperse, C. P. J. Am. Chem. Soc. 2005, 127, 5764.
6. (a) Young, I. S.; Kerr, M. A. J. Am. Chem. Soc. 2007, 129, 1465.
7. (b) Carson, C. A.; Kerr, M. A. Angew. Chem., Int. Ed. 2006, 45, 6560.
8. Wanapun, D.; Van Gorp, K. A.; Mosey, N. J.; Kerr, M. A.; Woo, T. K. Can. J. Chem. 2005, 83, 1752-1767.
9. Stereochemistry of all compounds was unambiguously confirmed by either X-ray crystallographic analysis or NOE analysis. See Supporting Information for details.
10. It should be noted that we are assuming that the stereochemical integrity of the nitrone iminium bond (Z-geometry) is maintained during the course of the reaction. While the Z-geometry is preferred for nitrones, it cannot be ruled out that the iminium geometry is fluxional under the reaction conditions.
11. Dolbier, W. S.; Wicks, G. E. J. Am. Chem. Soc. 1985, 107, 3626.