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

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 v...

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Published in:Angewandte Chemie International Edition 2018-11, Vol.57 (46), p.15217-15221
Main Authors: Fu, Zhengyan, Deng, Ning, Su, Sheng‐Nan, Li, Hongyang, Li, Ren‐Zhe, Zhang, Xia, Liu, Jie, Niu, Dawen
Format: Article
Language:English
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201809391