Silanediol Hydrogen Bonding Activation of Carbonyl Compounds

Geo-inspired activation: The first example of silanediols activating amide and aldehyde substrates through hydrogen bonding is described. Both NMR and X-ray co-crystallization studies demonstrate binding modes and affinity, and show that silanediol hydrogen-bonding assemblies can be modulated by the addition of carbonyl compounds. These silanols show catalysis in a Diels–Alder reaction and provide insight into the design of new organocatalysts (see figure).