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Kinetic Resolution of Tertiary Benzyl Alcohols via Palladium/Chiral Norbornene Cooperative Catalysis
Author(s) -
Hua Yu,
Liu ZeShui,
Xie PeiPei,
Ding Bo,
Cheng HongGang,
Hong Xin,
Zhou Qianghui
Publication year - 2021
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.202103428
Subject(s) - kinetic resolution , norbornene , chemistry , palladium , enantioselective synthesis , aryl , catalysis , reagent , chirality (physics) , combinatorial chemistry , selectivity , organic chemistry , tertiary alcohols , chiral symmetry breaking , polymer , alkyl , monomer , physics , quantum mechanics , quark , nambu–jona lasinio model
Herein we report a highly enantioselective kinetic resolution of tertiary benzyl alcohols via palladium/chiral norbornene cooperative catalysis. With simple aryl iodides as the resolution reagent, a wide range of readily available racemic tertiary benzyl alcohols are applicable to this method. Both chiral tertiary benzyl alcohols and benzo[ c ]chromene products are obtained in good to excellent enantioselectivities (selectivity factor up to 544). The appealing synthetic utility of the obtained enantioenriched tertiary alcohols is demonstrated by the facile preparation of several valuable chiral heterocycles. Preliminary mechanism studies include DFT calculations to explain the origin of enantiodiscrimination and control experiments to uncover the formation of a transient axial chirality during the kinetic resolution step.