Publication | Closed Access
Enantiopure α-Silyl-Substituted α-Hydroxyacetic Acids Using O-H Insertion Methodology and Boron-Based Asymmetric Reductions
20
Citations
0
References
2005
Year
Benzyl 2-Silyl-2-oxoacetatesBoron-based Asymmetric ReductionsBioorganic ChemistryEngineeringCorresponding α-Hydroxy EstersNatural SciencesOrganic ChemistryBenzyl 2-Silyl-2-diazoacetatesStereoselective SynthesisChemistryHeterocycle ChemistryPharmacologyAsymmetric CatalysisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
Two routes to optically active α-silyl-substituted α-hydroxyacetic acids are described. As a key step, the first utilizes O-H insertion reactions of (R)-and (S)-phenylethanol into benzyl 2-silyl-2-diazoacetates in the presence of [Rh2(OAc)4]. Alternatively, asymmetric reductions of benzyl 2-silyl-2-oxoacetates using (R)-Alpine-Borane® afford the corresponding α-hydroxy esters with up to 91% ee.