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Enantioselective Allylic C−H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis
Author(s) -
Ammann Stephen E.,
Liu Wei,
White M. Christina
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201603576
Subject(s) - enantioselective synthesis , allylic rearrangement , palladium , sulfoxide , chemistry , olefin fiber , oxazoline , catalysis , ligand (biochemistry) , asymmetric induction , aryl , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , alkyl , receptor
The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)‐catalyzed allylic C−H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide‐oxazoline (ArSOX) ligand. The allylic C−H oxidation reaction proceeds with the broadest scope and highest levels of asymmetric induction reported to date (avg. 92 % ee , 13 examples with greater than 90 % ee ).
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