Enantioselective Allylic C−H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis | Zendy

Ammann Stephen E. | Zendy; Liu Wei | Zendy; White M. Christina | Zendy

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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 , catalysis , chemistry , organic chemistry

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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