Synthesis 2008(7): 1153-1157  
DOI: 10.1055/s-2007-990935
PSP
© Georg Thieme Verlag Stuttgart · New York

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;
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Publikationsverlauf

Received 16 August 2007
Publikationsdatum:
28. November 2007 (online)

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.