Synthesis and Application of a New Cyclic Phosphoric Acid in Enantioselective Three-Component Mannich Reactions
Giovanni Ghigo, Alessio Robiolio Bose, Stefano Dughera
TL;DR
Scientists created a new chiral phosphoric acid catalyst that efficiently promotes a specific chemical reaction with high enantioselectivity.
Contribution
A new cyclic phosphoric acid was synthesized and shown to catalyze enantioselective three-component Mannich reactions effectively.
Findings
The catalyst achieved up to 89% enantiomeric excess in the reactions.
A three-step synthesis route was developed for the chiral phosphoric acid.
DFT calculations were used to study the catalytic mechanism.
Abstract
A novel point-chiral six-membered cyclic phosphoric acid was synthesized starting from an enantiopure precursor via a concise three-step route. Its catalytic performance was evaluated in enantioselective three-component Mannich reactions. Under optimized conditions, the catalyst provided good yields and satisfactory enantiomeric excesses (up to 89%). The basic mechanism of the catalysis was also studied by the DFT method.
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Taxonomy
TopicsAsymmetric Synthesis and Catalysis · Synthetic Organic Chemistry Methods · Axial and Atropisomeric Chirality Synthesis