Oxidative Kinetic Resolution of Cyclic Benzylic Ethers. (28th October 2020)

• Record Type: Journal Article
• Authors: Sun, Shutao; Ma, Yingang; Liu, Ziqiang; Liu, Lei
• Is Part Of: Angewandte Chemie. Volume 133:Number 1(2020)
• Page Start: 178
• Page End: 182
• Publication Date: 2020-10-28
• Subjects: asymmetric C−H oxidation -- cyclic benzylic ethers -- kinetic resolution -- late-stage oxidation -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202009594
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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. Abstract : A manganese‐catalyzed kinetic resolution through asymmetric C(sp 3 )−H oxidation was applied to a wide range of five‐membered 1, 3‐dihydroisobenzofurans and 2, 3‐dihydrobenzofurans as well as six‐membered 6 H ‐benzo[ c ]chromenes bearing diverse α‐substituents with extremely efficient enantiodiscrimination (see scheme). Late‐stage oxidative kinetic resolution of bioactive molecules that are otherwise difficult to access was further demonstrated.