Enantioselective reductive conjugate alkenylation of α,β-enones with keto alkenyl acetates by nickel catalysis

Reactions involving alkenyl acetates offer cost-effective and environmentally friendly routes for alkene synthesis, yet their asymmetric variant remains elusive. Concurrently, asymmetric conjugate alkenylation predominantly centered on nucleophilic addition using alkenyl—M. This manuscript presents...

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Bibliographic Details
Published in:Science China. Chemistry 2025, Vol.68 (1), p.157-162
Main Authors: He, Rong-De, Luo, Yun-Lei, Pan, Qiu-Quan, Yao, Qi-Wei, Shu, Xing-Zhong
Format: Article
Language:English
Subjects:
Acetates
Asymmetry
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Communications
Conjugates
Diketones
Enantiomers
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Summary:Reactions involving alkenyl acetates offer cost-effective and environmentally friendly routes for alkene synthesis, yet their asymmetric variant remains elusive. Concurrently, asymmetric conjugate alkenylation predominantly centered on nucleophilic addition using alkenyl—M. This manuscript presents an asymmetric reductive conjugate alkenylation reaction involving alkenyl acetates. The method facilitates the enantioselective addition of keto alkenyl groups to α,β-enones, resulting in the formation of unsaturated diketones—a class of useful structural motifs that are challenging to access otherwise. The use of electron-rich Pyroxy ligand is essential for achieving both high reaction efficiency and enantioselectivity.
ISSN:1674-7291
1869-1870
DOI:10.1007/s11426-024-2181-5