Carbohydrate-derived aminoalcohol ligands for asymmetric Reformatsky reactions

[Display omitted] Members of a family of functionally and stereochemically diverse d-glucosamine-derived tertiary aminoalcohol ligands have been used to promote the asymmetric Reformatsky reaction. The β-hydroxyester product tert-butyl 3-phenyl-3-hydroxy-propanoate was obtained enriched in either th...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 16; no. 1; pp. 213 - 221
Main Authors Emmerson, Daniel P.G., Hems, William P., Davis, Benjamin G.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.01.2005
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
TRANSFORMATION
REAGENT
BETA-HYDROXY ESTERS
CATALYSIS
CHIRAL LIGANDS
AMINO-ALCOHOLS
D-GLUCOSAMINE
SUGARS
DERIVATIVES
SELECTIVITY
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Summary:[Display omitted] Members of a family of functionally and stereochemically diverse d-glucosamine-derived tertiary aminoalcohol ligands have been used to promote the asymmetric Reformatsky reaction. The β-hydroxyester product tert-butyl 3-phenyl-3-hydroxy-propanoate was obtained enriched in either the (+)-( R) (up to 74% ee) or (−)-( S) (up to 42% ee) enantiomer depending on the choice of ligand. Although the selectivities are modest in absolute terms they represent some the better selectivities obtained to date for this reaction. A 1H NMR study was conducted to investigate this selectivity and suggested a secondary binding mode between ligand and zinc in addition to the expected N-2, O-3 coordination.
Bibliography:researchfish
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2004.11.049