6533b871fe1ef96bd12d2380

RESEARCH PRODUCT

Synthesis of (S)-(+)-sotalol and (R)-(−)-isoproterenol via a catalytic enantioselective Henry reaction

Victor Hernandez‐olmosGonzalo BlayJosé R. Pedro

subject

chemistry.chemical_classificationNitroaldol reactionStereochemistryOrganic ChemistryEnantioselective synthesisAlkylationAldehydeCatalysisCatalysisInorganic ChemistrychemistryNitroAmine gas treatingPhysical and Theoretical ChemistryEnantiomer

description

Abstract A unified approach for the synthesis of ( S )-(+)-sotalol and ( R )-(−)-isoproterenol has been developed. The enantioselective Henry reaction of the appropriate aldehyde in the presence of a camphor-derived amino pyridine–Cu(II) complex was the key step of the synthesis. The reduction of the nitro group to give the corresponding amino alcohols followed by reductive alkylation of the amine provided the target products with high enantiomeric excesses.

https://doi.org/10.1016/j.tetasy.2010.02.027