Palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with imines

Journal of the American Chemical Society

Volumn 129, Issue 41, 2007, Pages 12398-12399

  Trost, Barry M ^a   Silverman, Steven M ^a   Stambuli, James P ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE; IMINE; PALLADIUM; TRIMETHYLENEMETHANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLOADDITION; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; IMINES; METHANE; METHYLATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PALLADIUM;

EID: 35348988125     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0753389     Document Type: Article

References (11)

1. O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435.
2. Harwood, L. M.; Vickers, R. J. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; John Wiley & Sons, Inc.: New York, 2002; pp 169-252.
3. Yamago, S. Org. React. 2002, 61, 1.
4. (a) Jones, M. D.; Kemmitt, R. D. W. J. Chem. Soc., Chem. Commun. 1986, 1201.
5. (b) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636.
6. (c) Yamago, S.; Nakamura, M.; Wang, X.-Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694.
7. Trost, B. M.; Stambuli, J. P.; Silverman, S. M.; Schwörer, U. J. Am. Chem. Soc. 2006, 128, 13328.
8. Feringa, B. L. Acc. Chem. Res. 2000, 33, 346.
9. Alexakis, A.; Polet, D. Org. Lett. 2005, 7, 1621.
10. Choi, Y. H.; Choi, J. Y.; Yang, H. Y.; Kim, Y. H. Tetrahedron: Asymmetry 2002, 13, 801.
11. Our initial studies of TMM reactions of aliphatic N-aryl imines afforded complex mixtures of products. Work in this area is ongoing.