Asymmetric amination of cyclic β-keto esters catalyzed by amine-thiourea bearing multiple hydrogen bonding donors
نویسندگان
چکیده
منابع مشابه
Organocatalytic asymmetric Henry reaction of 1H-pyrrole-2,3-diones with bifunctional amine-thiourea catalysts bearing multiple hydrogen-bond donors
For the first time, a catalytic asymmetric Henry reaction of 1H-pyrrole-2,3-diones was achieved with a chiral bifunctional amine-thiourea as a catalyst possessing multiple hydrogen-bond donors. With this developed method, a range of 3-hydroxy-3-nitromethyl-1H-pyrrol-2(3H)-ones bearing quaternary stereocenters were obtained in acceptable yield (up to 75%) and enantioselectivity (up to 73% ee).
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New bifunctional organocatalysts amine-thioureas bearing multiple hydrogen bonding donors were synthesized and applied in catalytic asymmetric Michael addition of acetylacetone to aryl and alkyl nitroolefins. Multiple hydrogen bonding donors play a significant role in accelerating reactions, improving yields and enantioselectivities.
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An asymmetric α-amination of β-keto esters with azodicarboxylate in the presence of a guanidine-bisurea bifunctional organocatalyst was investigated. The α-amination products were obtained in up to 99% yield with up to 94% ee.
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Chalcones are still challenge substrates in Michael reactions, and only limited success has been achieved. This work describes a highly enantioselective Michael addition of diethyl malonate with chalcones catalyzed by cinchona alkaloids-derivatived bifunctional tertiary amine-thioureas bearing multiple hydrogen-bonding donors.
متن کاملCopper-catalyzed cascade reactions of α,β-unsaturated esters with keto esters
A copper-catalyzed cascade reaction of α,β-unsaturated esters with keto esters is reported. It features a copper-catalyzed reductive aldolization followed by a lactonization. This method provides a facile approach to prepare γ-carboxymethyl-γ-lactones and δ-carboxymethyl-δ-lactones under mild reaction conditions.
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ژورنال
عنوان ژورنال: Arkivoc
سال: 2010
ISSN: 1551-7012
DOI: 10.3998/ark.5550190.0012.211