C. Birk, J. Voss
Sep 23, 1996
Citations
0
Influential Citations
18
Citations
Journal
Tetrahedron
Abstract
Abstract 1-[3-Methyl-2-(2-thiolanylthio)butyl]piperidine ( 8 ) is obtained from L-valine via enantiomerically pure 1-(2-mercapto-3-methylbutyl)piperidine ( 6 ). The diastereoisomers are separated by column chromatography and the reactions of the carbanion 8a with electrophiles are studied. Semicyclic dithioacetals 12 – 15 are converted into the corresponding carbonyl compounds with [bis(trifluoroacetoxy)iodo]benzene (PIFA). Phenyl dichlorophosphate (PDCP) in the presence of sodium iodide and DMF is found to be a reagent for selective cleavage of the exocyclic CS bond. By using DOWEX 50W and paraformaldehyde in acetone/water a cleavage of both acetalic CS bonds is achieved in certain cases.