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

A.L. Braga, R.M. Rubim, H.S. Schrekker, L.A. Wessjohann, M.W.G. de Bolster, G. Zeni, J.A. Sehnem

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

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. © 2003 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)3291-3295
Number of pages4
JournalTetrahedron: Asymmetry
Volume14
DOIs
Publication statusPublished - 2003

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