Advanced Synthesis & Catalysis · 2002 · 179 citations · 0 references
Natural SciencesBiochemistryChemistryBiocatalysisEnzymologyOrganic ChemistryBiocatalytic StereoselectivityCatalytic MechanismsEnzymatic CatalysisOrganic SynthesisAldehydesBond Formation MechanismsChiral Product SynthesisEnantioselective CatalysisEnantioselective SynthesisEnzymatic SynthesisKetonesStereoselective Synthesis
(R)-Benzoins and (R)-2-hydroxypropiophenone derivatives are formed on a preparative scale by benzaldehyde lyase (BAL)-catalyzed C−C bond formation from aromatic aldehydes and acetaldehyde in aqueous buffer/DMSO solution with remarkable ease in high chemical yield and high optical purity. The substrate range of this thiamin diphosphate-dependent enzyme was examined with respect to a broad applicability of this benzoin condensation-type reaction in stereoselective synthesis.