Kinetic Resolution of -Allylic Pyrazoles via Photoexcited Chiral Copper Complex-Catalyzed Alkene → Isomerization.

Org Lett

State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023 (China).

Published: June 2024

Herein, we present an efficient and practical kinetic resolution (KR) of racemic allylic pyrazoles utilizing photoexcited chiral-copper-complex-mediated alkene → isomerization. This method enables the synthesis of both enantioenriched - and -allylic pyrazoles, achieving enantiomeric excesses (e.e.) of up to 97% and selectivity factors ( factors) as high as 217. Remarkably, the method's ability to furnish allylic pyrazoles with the -configuration, which is notably arduous to obtain under thermodynamic control, underscores the transformative potential of this synthetic protocol.

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http://dx.doi.org/10.1021/acs.orglett.4c01220DOI Listing

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