6533b7dcfe1ef96bd1272c3b
RESEARCH PRODUCT
Base-catalyzed isomerization of 2-isoxazolines enables a two-step enantioselective synthesis of β-hydroxynitriles from enals.
Jun LiuAntti PohjakallioPetri M. Pihkosubject
chemistry.chemical_classificationAldehydesMolecular StructureChemistryOrganic ChemistryEnantioselective synthesisStereoisomerismStereoisomerismIsoxazolesChemical synthesisAldehydeCatalysisCatalysischemistry.chemical_compoundCyclizationNitrilesEthylaminesOrganic chemistryOrganic synthesisEnantiomerIsomerizationdescription
The asymmetric synthesis of β-hydroxynitriles remains a challenge in organic synthesis. Herein we report a convenient synthesis of β-hydroxynitriles from enantiomerically enriched 3-unsubstituted 2-isoxazolines via a base-catalyzed ring-opening reaction that takes place without loss of enantiopurity. In combination with organocatalytic enantioselective synthesis of 3-unsubstituted 2-isoxazolines, the ring-opening enables a short 2-step synthesis of β-hydroxynitriles from α,β-unsaturated aldehydes in high enantiomeric purity.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-09-08 | The Journal of organic chemistry |