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Content archived on 2024-05-29

Bi-functional Cinchona Alkaloid derived Organocatalysts and their reactions


Bifunctional catalysts operate in a similar fashion to enzymes by simultaneously activating both substrate and reagent and promoting a reaction where the stereochemical outcome is controlled.

As both substrate and reagent are simultaneously activated, many new types of stereoselective reaction are waiting to be discovered.

In this proposal, we 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 enantioselective 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 block s for the synthesis of natural products and drug compounds is phenomenal. The chemistry proposed is built on solid and exciting preliminary results.

Unlike traditional metal ion catalysed reactions, the attraction of reactions catalysed by bifunctional org anocatalystsis 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 optimization 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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Oxford Road
United Kingdom

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