Photocatalysis and Kinetic Resolution by Lithiation to Give Enantioenriched 2-Arylpiperazines Article Swipe
Related Concepts
Chemistry
Kinetic resolution
Photocatalysis
Kinetic energy
Resolution (logic)
Combinatorial chemistry
Optically active
Enantioselective synthesis
Organic chemistry
Catalysis
Computer science
Artificial intelligence
Physics
Quantum mechanics
Anjan Kumar Das
,
Anthony Choi
,
Iain Coldham
·
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.1021/acs.orglett.3c00074
· OA: W4319057692
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.1021/acs.orglett.3c00074
· OA: W4319057692
Piperazines are important heterocycles in drug compounds. We report the asymmetric synthesis of arylpiperazines by photocatalytic decarboxylative arylation (metallaphotoredox catalysis) then kinetic resolution using <i>n</i>-BuLi/(+)-sparteine. This gave a range of piperazines with very high enantioselectivities. Further functionalizations gave enantioenriched 2,2-disubstituted piperazines, and either N-substituent can be removed selectively. Late-stage functionalizations of enantioenriched piperazine derivatives were demonstrated, including synthesis of a drug compound with glycogen synthase kinase (GSK)-3β inhibitor activity with potential for treating Alzheimer's disease.
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