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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For related syntheses of N-acyl- and N-boc-2-benzylpyrrolidines, see: Bertrand MB, Wolfe JP. Tetrahedron. 2005 In Press.
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