Diastereo‐ and Enantioselective Propargylation of 5H‐Thiazol‐4‐ones and 5H‐Oxazol‐4‐ones as Enabled by Cu/Zn and Cu/Ti Catalysis

Reported is the asymmetric propargylic substitution (APS) reaction of 5H‐thiazol‐4‐ones using a Cu/Zn dual metal catalytic system and the APS reaction of 5H‐oxazol‐4‐ones using a Cu/Ti catalytic system. These reactions furnish functional‐group‐rich, terminal‐alkyne‐containing products with two vicin...

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Bibliographic Details
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
Subjects:
Alkynes
Catalysis
Chemical reactions
Copper
Enantiomers
enantioselectivity
heterocycles
Metals
Oxazol
propargylation
Selectivity
Substitution reactions
synthetic methods
Titanium
Zinc
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Summary:Reported is the asymmetric propargylic substitution (APS) reaction of 5H‐thiazol‐4‐ones using a Cu/Zn dual metal catalytic system and the APS reaction of 5H‐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. ‘CuTi' pie: Cu/Zn and Cu/Ti dual metal systems have been devised to achieve the highly diastereo‐ and enantioselective propargylic substitution of 5H‐thiazol‐4‐ones and 5H‐oxazol‐4‐ones, respectively. These reactions demonstrate substantial substrate scope, giving terminal‐alkyne‐containing, functional‐group‐rich products in high yields.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201809391