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Asymmetric Bifunctional Organocatalysts and their Application in Organic Synthesis


We propose to introduce a new family of asymmetric bifunctional organocatalysts, which benefit from a strong Lewis basic site and a strong hydrogen donor group coupled to a rigid chiral scaffold originating from a cinchona alkaloid backbone. Such catalysts should be capable of not only promoting highly enantio-selective reactions of acidic pro-nucleophiles (such as malonate esters) to reactive Michael acceptors (such as nitro olefins), but have the power to promote reactions between less reactive reagents (such as to alpha, beta-unsaturated ketones, esters, imides).

If this is the case, then the implications of the chemistry for the synthesis of important enantioenriched building blocks for the synthesis of natural products and drug compounds is phenomenal. Unlike traditional metal ion catalysed reactions, the attraction of reactions catalysed by bifunctional organocatalysts is in the technical simplicity of performing, monitoring, sampling and working-up the reactions to give the desired products. Glove box techniques are not required, variables associated with the metal ions (counterions, impurities, toxicity, disposal) are not introduced and moisture or oxygen sensitivity is not an issue. These benefits allow for rapid identification and optimisation of the catalysts in the reactions and bode well for the use of the reactions in the pharmaceutical and related industries and academia alike.

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