Chiral Bifunctional Squaramide-Catalyzed Highly Enantioselective Michael Addition of Allomaltol to [beta],[gamma]-Unsaturated [alpha]-Ketoesters

A highly enantioselective Michael addition of allomaltol (5-hydroxy-2-methyl-4H-pyran-4-one) to both aromatic and aliphatic [beta],[gamma]-unsaturated [alpha]-ketoesters has been realized. Under the catalysis of a chiral bifunctional tertiary amine-squaramide that bears a (1R,2R)-1,2-diphenylethane-...

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Published inChemCatChem Vol. 6; no. 8; p. 2298
Main Authors Liu, Yunting, Wang, Qiaohui, Wang, Youming, Song, Haibin, Zhou, Zhenghong
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.08.2014
Subjects
Beta
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Summary:A highly enantioselective Michael addition of allomaltol (5-hydroxy-2-methyl-4H-pyran-4-one) to both aromatic and aliphatic [beta],[gamma]-unsaturated [alpha]-ketoesters has been realized. Under the catalysis of a chiral bifunctional tertiary amine-squaramide that bears a (1R,2R)-1,2-diphenylethane-1,2-diamine scaffold, the reaction proceeded smoothly with high levels of enantioselectivity to give the desired products in acceptable yields with 86->99% enantiomeric excess. This methodology provided an efficient process for the enantioselective synthesis of optically active kojic acid derivatives.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201402168