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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 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.201603576
Subject(s) - allylic rearrangement , enantioselective synthesis , palladium , sulfoxide , olefin fiber , oxazoline , catalysis , chemistry , ligand (biochemistry) , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , 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 ).