198198-50-4Relevant articles and documents
Stereocontrolled Synthesis of trans-3-Hydroxypipecolic Acids and Application to (-)-Swainsonine
Ferreira, Franck,Greck, Christine,Genet, Jean Pierre
, p. 615 - 622 (2007/10/03)
The enantioselective synthesis of both enantiomers of trans-3-hydroxypipecolic acid are described from a prochiral starting material: the methyl 3-oxo-7-methyloct-6-enoate.The stereocenters of the piperidine ring are created by enantioselective hydrogenation of the β-ketoester and by diastereoselective electrophilic amination of the β-hydroxyester enolate. (2R,3R)-3-Hydroxypipecolic acid methyl ester is the precursor for the synthesis of (-)-swainsonine. - Keywords: piperidine; indolizidine; chiral ruthenium complex; electrophilic amination.