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Palladium‐Catalyzed Synthesis of N ‐Aryl Pyrrolidines from γ‐( N ‐Arylamino) Alkenes: Evidence for Chemoselective Alkene Insertion into PdN Bonds
Author(s) -
Ney Joshua E.,
Wolfe John P.
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200460060
Subject(s) - alkene , intramolecular force , chemistry , aryl , palladium , pyrrolidine , medicinal chemistry , stereoselectivity , catalysis , butane , stereochemistry , organic chemistry , alkyl
The formation of a CC and a CN bond in a reaction between γ‐( N ‐arylamino) alkenes and aryl bromides results in the stereoselective synthesis of substituted pyrrolidine derivatives (see scheme). Preliminary studies suggest these reactions proceed by intramolecular alkene insertion into the PdN bond of intermediate [Pd(Ar)(amido)] complexes. dba=dibenzylideneacetone, dppb=1,3‐bis(diphenylphosphanyl)butane.