Buchler Glossary

Cupreidine (CAS-No. 70877-75-7)

Cupreidine Base (CAS-No. 70877-75-7), as well as the pseudoenantiomer Cupreine, belong to an emerging class of bifunctional highly enantioselective organocatalysts. They can be used for a wide range of asymmetric reactions.

Similar to the amino group of  6´-Aminocinchonine the hydroxy group proves crucial to obtain high enantioselectivity in many synthetically relevant reactions like Michael additions, Henry, Diels-Alder, Friedel-Crafts, Fluorination, Amination, Alkylation, Bromolactonization etc. despite its position far away from the stereocenters. Usually the electrophile is activated via the C6`-hydroxy group. On the other hand the free C6’ hydroxy group can be further functionalized to improve catalytic performance. The key step of Indoxacarb is a α-hydroxylation of a β-ketoester. Higher enantiomeric excesses can be obtained with Cupreidine compared to Cinchonine. Cupreidine as a derivative of Quinidine is also widely used as a racemic resolution agent.

For more detailed information about the application of Cupreidine (CAS-No. 70877-75-7) please enter into our free of charge chiral catalyst database.

Cupreidine (CAS-No. 70877-75-7)

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