The facile synthesis of chiral oxazoline catalysts for the diethylzinc addition to aldehydes

A range of chiral 4-(1′-hydroxyalkyl)oxazoline catalysts can be obtained in a straightforward two step synthesis, starting from β-hydroxy amino acids like l-serine or l-threonine. Catalyst 4c forms a complex with diethylzinc, effective for the enantioselective addition to aldehydes resulting in high...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2003-10, Vol.14 (21), p.3291-3295
Main Authors: Braga, Antonio L., Rubim, Rodrigo M., Schrekker, Henri S., Wessjohann, Ludger A., de Bolster, Martin W.G., Zeni, Gilson, Sehnem, Jasquer A.
Format: Article
Language:English
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Summary:A range of chiral 4-(1′-hydroxyalkyl)oxazoline catalysts can be obtained in a straightforward two step synthesis, starting from β-hydroxy amino acids like l-serine or l-threonine. Catalyst 4c forms a complex with diethylzinc, effective for the enantioselective addition to aldehydes resulting in high yields and enantiomeric excesses up to >99% even with aliphatic aldehydes. In the latter case the enantiomeric excess showed a marked dependence of the aldehyde's chain length. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2003.08.029