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Diastereo‐ and Enantioselective Propargylation of 5 H ‐Thiazol‐4‐ones and 5 H ‐Oxazol‐4‐ones as Enabled by Cu/Zn and Cu/Ti Catalysis
Author(s) -
Fu Zhengyan,
Deng Ning,
Su ShengNan,
Li Hongyang,
Li RenZhe,
Zhang Xia,
Liu Jie,
Niu Dawen
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201809391
Subject(s) - stereocenter , catalysis , vicinal , alkyne , enantioselective synthesis , chemistry , copper , combinatorial chemistry , metal , selectivity , dual (grammatical number) , dual role , medicinal chemistry , organic chemistry , art , literature
Reported is the asymmetric propargylic substitution (APS) reaction of 5 H ‐thiazol‐4‐ones using a Cu/Zn dual metal catalytic system and the APS reaction of 5 H ‐oxazol‐4‐ones using a Cu/Ti catalytic system. These reactions furnish functional‐group‐rich, terminal‐alkyne‐containing products with two vicinal stereocenters in high yields and with good to excellent diastereo‐ and enantioselectivities. This study demonstrates the use of dual metal catalytic systems as a viable approach to improve the selectivity profiles of the copper‐catalyzed APS reactions.