Organocatalysis - Aldol Reaction

Proline-Catalysed Aldol Reaction

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Sn2

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The initial interaction between proline and acetone generates an enamine intermediate, which then reacts further with an aldehyde to yield the aldol product. The reaction is controlled by a hydrogen-bonded transition state in which the aldehyde substituent occupies an equatorial position on the chair-like structure. The product is obtained in high enantioselectivity due to the proline catalyst.