Journal of the American Chemical Society · 2005 · 235 citations · 20 references
Natural SciencesChemistryBiocatalysisCatalysisOrganic ChemistryCatalyst DesignCatalytic MechanismsChiral SeparationHeterocycle SynthesisOrganic SynthesisAldehydesAsymmetric CatalysisEnantioselective CatalysisEnantioselective SynthesisHydrogen BondingLewis Acid CatalysisLewis AcidityMolecular Catalysts
Axially chiral 1,1'-biaryl-2,2'-dimethanol (3, BAMOL) family of diols are highly effective catalysts for enantioselective hetero-Diels-Alder reactions between aminosiloxydiene 1 and a wide variety of unactivated aldehydes. The reactions proceed in useful yields and excellent enantioselectivities. The diols function in the same capacity as Lewis acids, by activating the aldehyde carbonyl group through hydrogen bonding.
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The Hydrogen Bond in the Solid State
Thomas Steiner · Angewandte Chemie International Edition · 2002 · 6.2K citations