Catalytic, Three-Component Assembly Reaction for the Synthesis of Pyrrolidines

Organic Letters

Volumn 5, Issue 19, 2003, Pages 3487-3490

  Galliford, Chris V ^a   Beenen, Melissa A ^a   Nguyen, Sonbinh T ^a   Scheidt, Karl A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNE; ALPHA DIAZO ESTER; CHEMICAL COMPOUND; COPPER DERIVATIVE; ESTER DERIVATIVE; IMINE; METAL; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; DECOMPOSITION; POLARIZATION; PROTEIN ASSEMBLY; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 0344392778     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035292y     Document Type: Article

References (26)

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18. This process has been observed previously in the catalytic synthesis of aziridines from imines: (a) Bartnik, R.; Mloston, G. Tetrahedron 1984, 40, 2569-2576. (b) Hansen, K. B.; Finney, N. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. Engl. 1995, 34, 676-678.
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21. During the last stage of preparation of our manuscript, a related approach to pyrrolidines using Ru(CO)porphyrin catalysts appeared in the literature: Li, G.-Y.; Chen, J.; Yu, W.-Y.; Hong, W.; Che, C.-M. Org. Lett. 2003, 5, 2153-2156.
22. See Supporting Information for details.
23. Salomon, R. G.; Kochi, J. K. J. Am. Chem. Soc. 1973, 95, 1889-1897. Yield (eq 1) with 10 mol% commercial [CuOTf]: 10-25%
24. For an example of a nitro group binding to copper(I), see: Yokota, S.; Tachi, Y.; Nishiwaki, N.; Ariga, M.; Itoh, S. Inorg. Chem. 2001, 40, 5316-5317.
25. Yield suffers presumably due to the instability of the starting material imine under the reaction conditions.
26. Crystallographic data for 10 have been deposited with the Cambridge Crystallographic Data Centre. See Supporting Information for details.