Enantioselective construction of highly substituted pyrrolidines by palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with ketimines

Journal of the American Chemical Society

Volumn 132, Issue 24, 2010, Pages 8238-8240

  Trost, Barry M ^a   Silverman, Steven M ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

A-CARBON; ALLYL ACETATE; ASYMMETRIC ADDITION; ENANTIOSELECTIVE CONSTRUCTION; FUNCTIONALIZED; HETEROCYCLES; KETIMINES; PHOSPHORAMIDITE LIGANDS; PYRROLIDINES; TRIMETHYLENEMETHANE; TRIMETHYLSILYL;

TRANSITION METALS;

PALLADIUM;

IMINE; METHANE; PALLADIUM; PYRROLIDINE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; ENANTIOSELECTIVITY;

CATALYSIS; IMINES; METHANE; NITRILES; PALLADIUM; PYRROLIDINES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 77953646546     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja102102d     Document Type: Article

References (17)

1. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1
2. Trost, B. M. Pure Appl. Chem. 1988, 60, 1615
3. Lautens, M., Klute, W., and Tam, W. Chem. Rev. 1996, 96, 49
4. Yamago, S. and Nakamura, E. Org. React. 2002, 61, 1
5. Chan, D. M. T. Recent Advances in Palladium-Catalyzed Cycloadditions Involving Trimethylenemethane and its Analogs. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S. and Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; pp 57 - 83.
6. Trost, B. M., King, S. A., and Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902
7. Trost, B. M. and Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636
8. Trost, B. M. and Chan, D. M. T. J. Am. Chem. Soc. 1979, 101, 6429
9. Trost, B. M., Stambuli, J. P., Silverman, S. M., and Schwörer, U. J. Am. Chem. Soc. 2006, 128, 13328
10. Hayashi reported a single account of an asymmetric TMM reaction: Yamamoto, A., Ito, Y., and Hayashi, T. Tetrahedron Lett. 1989, 30, 375
11. Trost, B. M., Cramer, N., and Silverman, S. M. J. Am. Chem. Soc. 2007, 129, 12396
12. Trost, B. M., Silverman, S. M., and Stambuli, J. P. J. Am. Chem. Soc. 2007, 129, 12398
13. Trost, B. M., McDougall, P. J., Hartmann, O., and Wathen, P. T. J. Am. Chem. Soc. 2008, 130, 14960
14. Marquand, P. L. and Tam, W. Angew. Chem., Int. Ed. 2008, 47, 2926
15. Vilaivan, T., Bhanthumnavin, W., and Sritana-Anant, Y. Curr. Org. Chem. 2005, 9, 873
16. Shibasaki, M. and Motomu, K. Chem. Rev. 2008, 108, 2853
17. Semiempirical AM1 calculations performed using Spartan indicate an energy difference of 1.09 kcal/mol with epi-7 being the more stable isomer.