Abstract/Summary

The synthetic approach to threo-2-amino-3-hydroxyesters possessing long alkyl chains outlined herein centres on the generation of chiral azomethine ylids by reaction of (5R)-5-phenyl-morpholin-2-one, (R)-(1), with long chain aldehydes. In the presence of a second equivalent of aldehyde, the azomethine ylid can be trapped to afford a cycloadduct with three new stereodefined centres. Degradation of the cycloadduct allows entry to beta-substituted-alpha-amino acid derivatives, which have potential as building blocks for sphingosine synthesis.