Enantioselective synthesis of 3,4-dihydropyran derivatives via organocatalytic Michael reaction of α,β-unsaturated enones.

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ID: 98897
2012
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Ranked #25 of 103 articles by views in The Journal of organic chemistry

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Abstract
A simple chiral diamine catalyst (1a) was successfully applied in the asymmetric Michael reaction between cyclic dimedone and α,β-unsaturated ketones. Both acyclic enones with aryl or alkyl β-substituents and cyclic enones were tolerated well in the reaction. The desired adducts were obtained in high yields (up to 98%) with excellent enantioselectivities (up to 97% ee). The additives were found to increase the reactivity dramatically. The biologically active 2,4-disubstituted polyhydroquinoline scaffold was conveniently prepared through an ammoniation from the generated 3,4-dihydropyran product.
Reference Key
liu2012enantioselectivethe Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Liu, Yangbin;Liu, Xiaohua;Wang, Min;He, Peng;Lin, Lili;Feng, Xiaoming;
Journal The Journal of organic chemistry
Year 2012
DOI
10.1021/jo3001047
URL
Keywords
Antimicrobial activity multicomponent reaction antimalarial activity 5-imidazopyrazole incorporated polyhydroquinolines antituberculosis activity

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