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Dual Lewis acid - Lewis base activation in enantioselective additions to aldehydes
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2006
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Lewis Base ActivationAbstract ReactionEngineeringLewis Acidic TiOrganic ChemistryDual Lewis AcidCatalysisOrganometallic CatalysisChemistryEnantioselective AdditionsAsymmetric CatalysisEthyl CyanoformateEnantioselective SynthesisBiomolecular Engineering
Abstract Reaction of benzaldehyde with ethyl cyanoformate in the presence of Lewis acidic Ti(IV) complexes of bispyridylamide or salen ligands and Lewis basic amines affords the O -alkoxycarbonylated cyanohydrin. In the presence of the salen-based catalytic system, acetyl cyanide can also be added to benzaldehyde, providing a highly enantioselective direct route to the O -acetylated cyanohydrin.