The First Asymmetric Synthesis of 1,4-Dideoxy-1,4-imino-D-talitol

The first stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-Talitol has been achieved in 24% overall yield from conveniently protected (S)-glyceraldimine (1), which is easily prepared from inexpensive D-mannitol. The synthesis is based on the addition of vinylmagnesium bromide to this N-benzylimine followed by N-acylation, ring-closing metathesis and asymmetric dihydroxylation. In this synthesis as many as three stereogenic centres are constructed with total stereoselectivity.