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Catalytic Asymmetric Synthesis of Branched Chiral Allylic Phenyl Ethers from ( E )‐Allylic Alcohols
Author(s) -
Olson Angela C.,
Overman Larry E.,
Sneddon Helen F.,
Ziller Joseph W.
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900678
Subject(s) - chemistry , allylic rearrangement , oxazoline , catalysis , enantiomer , alkene , enantioselective synthesis , palladium , medicinal chemistry , carboxylate , organic chemistry , stereochemistry
The first di‐μ‐amidate dipalladium complexes and a new di‐μ‐carboxylate dipalladium complex of the COP (cobalt oxazoline palladacycle) palladium(II) catalyst family are reported and characterized crystallographically. The di‐μ‐amidate complex 3 and its enantiomer ( ent ‐ 3 ) are the first asymmetric catalysts that allow commercially available, or readily accessible, ( E )‐2‐alken‐1‐ols to be transformed to enantioenriched branched allylic aryl ethers upon reaction of their trichloroacetimidate derivatives with phenols. The 3‐aryloxy‐1‐alkene products are formed in high enantiomeric purity (typically 90–98% ee ) and useful yields (61–88%).