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RESEARCH PRODUCT
Diastereoselective formation of highly functionalised α-substituted amino acid derivatives via aldol addition
Kari RissanenMartin BrunnerAri M. P. KoskinenThomas StraubMaija Nissinensubject
chemistry.chemical_classificationStereochemistryOrganic ChemistryAbsolute configurationSolid-stateAnalytical ChemistryAmino acidInorganic ChemistrySerineAldol reactionchemistrySubstituted Amino AcidTwo-dimensional nuclear magnetic resonance spectroscopySpectroscopydescription
Abstract Highly diastereoselective aldol additions of (2 R ,4 S )-3- tert -butyl 4-methyl 2- tert -butyloxazolidine-3,4-dicarboxylate ( 1 ) are reported. The utility of the highly substituted oxazolidines of type 1 for diastereoselective α-addition of the fully protected amino acid l -serine with achiral and chiral carbonyl compounds is demonstrated and the relative and absolute configuration of the aldol products are discussed on the basis of NOESY data and solid state structures of selected examples. The aldol products represent highly useful intermediates in the syntheses of sphingosine-related metabolites.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2005-01-01 | Journal of Molecular Structure |