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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Aldehydes
aldehydes
catalysts
Catalysts
synthesis
Threonine
Chain length
Serine
amino acids
Amino acids
Amino Acids
diethylzinc

Cite this

Braga, A. L., Rubim, R. M., Schrekker, H. S., Wessjohann, L. A., de Bolster, M. W. G., Zeni, G., & Sehnem, J. A. (2003). The facile synthesis of chiral oxazoline catalysts for the diethylzinc addition to aldehydes. Tetrahedron: Asymmetry, 14, 3291-3295. https://doi.org/10.1016/j.tetasy.2003.08.029
Braga, A.L. ; Rubim, R.M. ; Schrekker, H.S. ; Wessjohann, L.A. ; de Bolster, M.W.G. ; Zeni, G. ; Sehnem, J.A. / The facile synthesis of chiral oxazoline catalysts for the diethylzinc addition to aldehydes. In: Tetrahedron: Asymmetry. 2003 ; Vol. 14. pp. 3291-3295.
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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. {\circledC} 2003 Elsevier Ltd. All rights reserved.",
author = "A.L. Braga and R.M. Rubim and H.S. Schrekker and L.A. Wessjohann and {de Bolster}, M.W.G. and G. Zeni and J.A. Sehnem",
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Braga, AL, Rubim, RM, Schrekker, HS, Wessjohann, LA, de Bolster, MWG, Zeni, G & Sehnem, JA 2003, 'The facile synthesis of chiral oxazoline catalysts for the diethylzinc addition to aldehydes' Tetrahedron: Asymmetry, vol. 14, pp. 3291-3295. https://doi.org/10.1016/j.tetasy.2003.08.029

The facile synthesis of chiral oxazoline catalysts for the diethylzinc addition to aldehydes. / Braga, A.L.; Rubim, R.M.; Schrekker, H.S.; Wessjohann, L.A.; de Bolster, M.W.G.; Zeni, G.; Sehnem, J.A.

In: Tetrahedron: Asymmetry, Vol. 14, 2003, p. 3291-3295.

Research output: Contribution to JournalArticleAcademicpeer-review

TY - JOUR

T1 - The facile synthesis of chiral oxazoline catalysts for the diethylzinc addition to aldehydes

AU - Braga, A.L.

AU - Rubim, R.M.

AU - Schrekker, H.S.

AU - Wessjohann, L.A.

AU - de Bolster, M.W.G.

AU - Zeni, G.

AU - Sehnem, J.A.

PY - 2003

Y1 - 2003

N2 - 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.

AB - 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.

U2 - 10.1016/j.tetasy.2003.08.029

DO - 10.1016/j.tetasy.2003.08.029

M3 - Article

VL - 14

SP - 3291

EP - 3295

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

SN - 0957-4166

ER -