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Synthesis 2008(7): 1153-1157
DOI: 10.1055/s-2007-990935
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
Further Information
Received
16 August 2007
Publication Date:
28 November 2007 (online)
Publication History
Publication Date:
28 November 2007 (online)
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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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