Synthesis of (R)- and (S)-3-(tert-butyldimethylsilyloxy)-1-pyrroline N- oxides - Chiral nitrones for synthesis of biologically active pyrrolidine derivative, Geissman-Waiss lactone

Article abstract of DOI:10.1016/S0040-4039(98)00333-5

Tungstate-catalyzed oxidation of O-tert-butyldimethylsilyl (O-TBDMS) protected (R)-3-hydroxypyrrolidine ((R)2), derived from trans-4-hydroxy-L- proline, gave O-TBDMS protected (R)-3-hydroxy-1-pyrroline N-oxide ((R)1), which is a new chiral precursor for the synthesis of Geissman-Waiss lactone. The enantiomeric nitrone (S)-1 was also prepared by the oxidation of (S)-2 derived from L-malic acid.