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Chemistry · L5 · Proline Organocatalysis: The Enamine Mechanism

The organocatalytic (metal-free) aldol pathway: proline condenses with an aldehyde donor to form an enamine, then its own carboxylic acid shields one face of that enamine, forcing the electrophilic acceptor to approach from the open face only.

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Aldehyde/ketone donor+ proline (chiral 2° amine)Condensation(iminium formation, − H2O)Enamine intermediatecarboxylic acid H-bonds to andshields one faceElectrophilic aldehydeacceptorAcceptor approachesfrom the open face onlyHydrolysis releases aldol product+ regenerates free proline

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