Organic Letters · 2001 · 193 citations · 30 references
Natural SciencesChemistryBiocatalysisCatalysisStructure-activity RelationshipsCatalyst DesignCatalyst PreparationCatalyst SynthesisCatalytic MechanismsAmino AcidsAsymmetric CatalysisAsymmetric Cross-couplingCatalyst Structure - Activity RelationshipsChiral Catalyst DesignEnantioselective CatalysisEnantioselective Catalyst DesignEnantioselective Synthesis
A series of chiral oxovanadium(IV) complexes derived from tridentate N-3,5-substituted and N-3,4-benzo- and N-5,6-benzo-salicylidene-alpha-amino acids can serve as efficient catalysts for the enantioselective oxidative couplings of various 3-, 6-, and 7-substituted 2-naphthols under O(2). The best scenario involves the use of a vanadyl complex arising from 2-hydroxy-1-naphthaldehyde and valine (or phenylalanine) in CCl(4), leading to BINOLs in good yields (75-100%) and with enantioselectivities of up to 68%.
30