Catalytic Enantioselective 5-Hydroxyisoxazolidine Synthesis: An Asymmetric Entry to β-Amino Acids

Ismail Ibrahem; Ramon Rios; Jan Vesely; Gui-Ling Zhao; Armando Córdova

doi:10.1055/s-2007-990935

PSP

Catalytic Enantioselective 5-Hydroxyisoxazolidine Synthesis: An Asymmetric Entry to β-Amino Acids

Ismail Ibrahem, Ramon Rios, Jan Vesely, Gui-Ling Zhao, Armando Córdova*
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden
Fax: +46(8)154908; e-Mail: acordova@organ.su.se;

Abstract

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Abstract

The highly chemo- and enantioselective organocatalytic tandem reaction between N-carbamate-protected hydroxylamines and α,β-unsaturated aldehydes is presented. The reaction represents a unique entry for the asymmetric synthesis of 5-hydroxyisoxazolidines, oxazolidin-5-ones or γ-hydroxyamino alcohols in high yields and 90-99% ee. A procedure for the conversion of the oxazolidin-5-ones into the corresponding β-amino acids is also described.

Key words

organocatalysis - amination reactions - β-amino acid synthesis - isoxazolidines - asymmetric catalysis

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References

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