ASYMMETRIC SYNTHESIS VIA HETEROCYCLIC INTERMEDIATES - XXXIX. ASYMMETRTIC SYNTHESIS OF (ENANTIOMERICALLY AND DIASTEREOMERICALLY VIRTUALLY PURE) METHYL 2-AMINO-4,5-EPOXY-3-HYDROXY-ALKANOATES AND METHYL 2-AMINO-3-HYDROXY-4,5-METHYLENE-ALKANOATES BY THE BISLA

Article abstract of DOI:10.1016/S0040-4020(01)86037-3

α,β-Unsaturated aldehydes react with the titanated bislactim ether 6 of cyclo-(L-val-gly) to give the (2R,1'S)-syn-addition products of type 8.With TBHP (catalyzed by Ti(OiPr)4 with and without (+)- or (-)-DET) these furnish the epoxides 10 or 11 with 1',