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Highly Enantioselective CuAAC of Functional Tertiary Alcohols Featuring an Ethynyl Group and Their Kinetic Resolution
Author(s) -
Liao Kui,
Gong Yi,
Zhu RenYi,
Wang Cai,
Zhou Feng,
Zhou Jian
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.202016286
Subject(s) - stereocenter , enantioselective synthesis , kinetic resolution , moiety , cycloaddition , chemistry , phosphonate , combinatorial chemistry , azide , stereochemistry , tertiary alcohols , catalysis , organic chemistry
The first highly enantioselective Cu I ‐catalyzed azide‐alkyne cycloaddition (CuAAC) of tertiary alcohols and their kinetic resolution is reported. This approach allows facile access to multifunctional tertiary alcohols featuring an α‐ethynyl or α‐triazole moiety, and represents the first successful kinetic resolution of racemates with a tetrasubstituted carbon stereocenter via CuAAC. Newly developed pyridinebisoxazoline (PYBOX) ligands with a C4 phosphonate group play a key role.