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Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones.


ABSTRACT: The organocatalytic Michael addition of malonates to symmetric unsaturated 1,4-diketones catalyzed by thiourea and squaramide derivatives with Cinchona alkaloids afforded the formation of a new C-C bond in high yields (up to 98%) and enantiomeric purities (up to 93%). The absolute configuration of the product was suggested from comparison of the experimental and calculated VCD spectra of the reaction product 3a.

SUBMITTER: Zari S 

PROVIDER: S-EPMC3458770 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones.

Zari Sergei S   Kailas Tiiu T   Kudrjashova Marina M   Oeren Mario M   Järving Ivar I   Tamm Toomas T   Lopp Margus M   Kanger Tõnis T  

Beilstein journal of organic chemistry 20120904


The organocatalytic Michael addition of malonates to symmetric unsaturated 1,4-diketones catalyzed by thiourea and squaramide derivatives with Cinchona alkaloids afforded the formation of a new C-C bond in high yields (up to 98%) and enantiomeric purities (up to 93%). The absolute configuration of the product was suggested from comparison of the experimental and calculated VCD spectra of the reaction product 3a. ...[more]

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