Preparation of enantiopure long chain threo-2-amino-3-hydroxyesters via chiral morpholinone-derived azomethine ylids

Brome, V.A., Harwood, L.M. ORCID: https://orcid.org/0000-0002-8442-7380 and Osborn, H.M.I. ORCID: https://orcid.org/0000-0002-0683-0457 (2006) Preparation of enantiopure long chain threo-2-amino-3-hydroxyesters via chiral morpholinone-derived azomethine ylids. Canadian Journal of Chemistry-Revue Canadienne De Chimie, 84 (10). pp. 1448-1455. ISSN 0008-4042 doi: 10.1139/v06-121

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.