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Catalytic Asymmetric Michael Addition of Malonate Derivatives to Chalcone

Author: ZhangXiaoLing
Tutor: ZhengYan
School: Tianjin University
Course: Organic Chemistry
Keywords: Chiral phase-transfer catalyst malonic esters N-acetylamino malonate chalcone Michael addition
CLC: TQ203.2
Type: Master's thesis
Year: 2010
Downloads: 19
Quote: 0
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Abstract


Recently, catalytic asymmetric Michael addition of carbon nucleophiles toα,β-unsaturated compounds has become an emerging field of organic chemistry. This significant protocol provides one of the most economical and efficient approaches for the carbon-carbon, carbon-heteroatom bond-forming. However, in terms of Michael addition reactions of malonic esters and their derivatives to chalcone, most chiral phase-transfer catalysts showed weak activity and enantioselectivity. Therefore, one crucial objective is the design and synthesis of new chiral phase-transfer catalyst.According to the analyses made above, we are ready to try the asymmetric Michael addition of malonic esters and N-acetylaminomalonate to chalcone. Two double-spiro chiral phase-transfer catalysts were synthesized from the optically pure 1,1’-binaphthol through four steps. Then, the model reaction of N-acetylamino- malonate to chalcone was carried out in the presence of the catalyst and gave the corresponding addition products with 81% yield, 59% ee.Furthermore, we choose the model reaction of dimethyl malonate to chalcone by the double-spiro chiral phase-transfer catalysts and other majorizations, giving high yield (up to 99%) and moderate enantioselectivities (up to 66% ee).

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