Asymmetric intermolecular aldol catalysed by proline

Sn2

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

Enantioselective intermolecular aldol catalysed by proline
Acetone and 2-methylpropanal

The reaction goes via an enamine, which attacks the aldehyde Re-face to form the R-product. In the transition state the isopropyl group is pseudoequatorial to minimise the 1,3-diaxial repulsions from the axial methyl group alpha to the nitrogen. This forms the R-aldol product.

Click for more information on Re and Si.

B. List, R. A. Lerner and C. F. Barbas, J. Am. Chem. Soc., 2000, 122, 2395–2396.

J. Liu and L. Wang, Synthesis (Stuttg)., 2016, 49, 960–972.

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