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

Brome, V.A., Harwood, L.M. and Osborn, H.M.I. (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

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To link to this article 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.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy
ID Code:13783
Uncontrolled Keywords:sphingosine, morpholinone, chiral azomethine ylid, dipolar cycloaddition, AMINO-ACID-DERIVATIVES, D-ERYTHRO-SPHINGOSINE, D-THREO-SPHINGOSINE, STEREOSELECTIVE SYNTHESIS, ENANTIOSELECTIVE SYNTHESIS, ASYMMETRIC, PRODUCTS, RELAY SYSTEM, MEMORY RELAY, D-GALACTOSE, L-SERINE

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