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Asymmetric Aldol Reaction of 3-Acetyl-2H-chromen-2-ones and Isatins Catalyzed by a Bifunctional Quinidine Urea Catalyst.


ABSTRACT: The asymmetric aldol reaction of 3-acetyl-2H-chromen-2-ones and isatins has been realized by using a bifunctional quinidine-derived urea as the catalyst. The corresponding 3-hydroxyoxindole derivatives containing a 2H-chromen-2-one moiety were obtained in good yields and high enantioselectivities. When (Z)-ethyl 2-benzylideneacetoacetate was used as the substrate, a mixture of two diastereomers (both Z and E) was obtained due to the isomerization of the double bond under the reaction conditions.

SUBMITTER: Abbaraju S 

PROVIDER: S-EPMC4019438 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Asymmetric Aldol Reaction of 3-Acetyl-2<i>H</i>-chromen-2-ones and Isatins Catalyzed by a Bifunctional Quinidine Urea Catalyst.

Abbaraju Santhi S   Zhao John Cong-Gui JC  

Advanced synthesis & catalysis 20140101 1


The asymmetric aldol reaction of 3-acetyl-2<i>H</i>-chromen-2-ones and isatins has been realized by using a bifunctional quinidine-derived urea as the catalyst. The corresponding 3-hydroxyoxindole derivatives containing a 2<i>H</i>-chromen-2-one moiety were obtained in good yields and high enantioselectivities. When (<i>Z</i>)-ethyl 2-benzylideneacetoacetate was used as the substrate, a mixture of two diastereomers (both <i>Z</i> and <i>E</i>) was obtained due to the isomerization of the double  ...[more]

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