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

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 gro...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 21; no. 5; pp. 578 - 581
Main Authors Blay, Gonzalo, Hernández-Olmos, Víctor, Pedro, José R.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.03.2010
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
PERFORMANCE LIQUID-CHROMATOGRAPHY
BETA-ADRENERGIC BLOCKERS
D-SOTALOL
ASYMMETRIC-SYNTHESIS
INDUCED MYOCARDIAL INJURY
COPPER(II)-IMINOPYRIDINE COMPLEXES
RESOLUTION
DRUGS
ISOPROTERENOL
DERIVATIZATION
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Summary: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.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2010.02.027