Palladium-catalyzed tandem N-arylation/carboamination reactions for the stereoselective synthesis of N-aryl-2-benzyl pyrrolidines
- PMID: 15957894
- PMCID: PMC2750836
- DOI: 10.1021/ol050647u
Palladium-catalyzed tandem N-arylation/carboamination reactions for the stereoselective synthesis of N-aryl-2-benzyl pyrrolidines
Abstract
[reaction: see text] The tandem N-arylation/carboamination of gamma-amino alkenes with two different aryl bromides provides rapid entry to differentially arylated N-aryl-2-benzyl pyrrolidine derivatives in good yields with good to excellent levels of diastereoselectivity. The selective diarylation is achieved in a one-pot process by an in situ modification of the palladium catalyst via phosphine ligand exchange.
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References
-
- Heumann A, Reglier M. Tetrahedron. 1996;52:9289.
- Malacria M. Chem. Rev. 1996;96:289. - PubMed
-
-
For recent examples, see: Ajamian A, Gleason JL. Angew. Chem., Int. Ed. 2004;43:3754. Yamamoto Y, Nakagai Y, Itoh K. Chem. Eur. J. 2004;10:231. Cossy J, Bargiggia F, BouzBouz S. Org. Lett. 2003;5:459. Thadani AN, Rawal VH. Org. Lett. 2002;4:4317. Son SU, Park KH, Chung YK. J. Am. Chem. Soc. 2002;124:6838. Louie J, Bielawski CW, Grubbs RH. J. Am. Chem. Soc. 2001;123:11312. Evans PA, Robinson JE. J. Am. Chem. Soc. 2001;123:4609.
-
-
- Ney JE, Wolfe JP. Angew. Chem., Int. Ed. 2004;43:3605. - PubMed
-
-
For related syntheses of N-acyl- and N-boc-2-benzylpyrrolidines, see: Bertrand MB, Wolfe JP. Tetrahedron. 2005 In Press.
-
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