Abstract
A stereodivergent synthesis of 1,4-dideoxy-1,4-imino- d-mannitol I and d-allitol III from an ( S)-glyceraldimine, which is easily prepared from d-mannitol, has been achieved with overall yields of 62% and 49%, respectively. The synthesis is based on the addition of vinylmagnesium bromide to N-benzylimine 1 , derived from readily available ( R)-2,3- O-isopropylideneglyceraldehyde, followed by N-allylation or N-acryloylation, ring-closing metathesis and asymmetric dihydroxylation.
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