Enantioselective Transfer Hydrogenation of Oxocarbenium Ions Enables Asymmetric Access to α-Substituted 1,3-Dihydroisobenzofurans
Reported here is an efficient enantioselective transfer hydrogenation of cyclic oxocarbenium ions generated in situ through collapse of the corresponding acetal substrates. The asymmetric approach provides straightforward access to a variety of chiral α-aryl substituted 1,3-dihydroisobenzofurans in high yields with excellent enantioselectivities. α-Alkynyl substituted 1,3-dihydroisobenzofurans were also proved to be suitable substrates. In addition, when the reaction was performed at gram scale, the desired product was obtained in good yields with excellent enantioselectivity.
Zhou, Likai,Jia, Kuiyong,Liu, Xigong,Liu, Lei
p. 421 - 428
(2021/10/01)
Oxidative Kinetic Resolution of Cyclic Benzylic Ethers
A manganese-catalyzed oxidative kinetic resolution of cyclic benzylic ethers through asymmetric C(sp3)?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.
Liu, Lei,Liu, Ziqiang,Ma, Yingang,Sun, Shutao
supporting information
p. 176 - 180
(2020/10/30)
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