Chiral synthesis of both enantiomers of 1,4-dideoxy-1,4-iminolyxitol and 1,4-dideoxy-1,4-iminoribitol

Article abstract of DOI:10.1016/S0957-4166(00)80499-1

Reaction of 2,3-dibromopropionyl chloride with 4-methoxyphenol and (S)-1-methylbenzylamine yielded a 4:5 mixture of readily separable diastereomeric aziridine esters in an excellent yield. Both diastereomers, upon heating with vinylene carbonate, furnished four readily separable diastereomeric pyrrolidine esters, respectively, which were transformed into both enantiomers of 1,4-dideoxy-1,4-iminolyxitol and 1,4-dideoxy-1,4-iminoribitol.