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Oxidative Kinetic Resolution of Cyclic Benzylic Ethers
Author(s) -
Sun Shutao,
Ma Yingang,
Liu Ziqiang,
Liu Lei
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202009594
Subject(s) - chemistry , kinetic resolution , substituent , oxidative phosphorylation , ether , kinetic energy , molecule , manganese , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , enantioselective synthesis , biochemistry , physics , quantum mechanics
A manganese‐catalyzed oxidative kinetic resolution of cyclic benzylic ethers through asymmetric C(sp 3 )−H oxidation is reported. The practical approach is applicable to a wide range of 1,3‐dihydroisobenzofurans bearing diverse functional groups and substituent patterns at the α position with extremely efficient enantiodiscrimination. The generality of the strategy was further demonstrated by efficient oxidative kinetic resolution of another type of five‐membered cyclic benzylic ether, 2,3‐dihydrobenzofurans, and six‐membered 6H‐benzo[c]chromenes. Direct late‐stage oxidative kinetic resolution of bioactive molecules that are otherwise difficult to access was further explored.