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A Practical Synthesis of Chiral Oxazolines through a Highly Diastereoselective Coupling–Cyclization Reaction of N ‐(Buta‐2,3‐dienyl)amides and Aryl Iodides
Author(s) -
Wang Nan,
Chen Bo,
Ma Shengming
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201400023
Subject(s) - chemistry , oxazoline , aryl , optically active , combinatorial chemistry , palladium , coupling reaction , reaction conditions , organic chemistry , catalysis , alkyl
A highly trans diastereoselective synthesis of 2,4,5‐trisubstituted oxazoline derivatives is described that proceeds through a palladium‐catalyzed coupling–cyclization reaction of N ‐(buta‐2,3‐dienyl)amides with aromatic iodides. The reaction with optically active substrates provides convenient access to highly enantioenriched oxazoline derivatives with excellent 1,2‐induction.