Abstract
AbstractAn improved and convenient preparation of protected (S)‐isoserinal on a large scale is reported. This key intermediate was reacted through organocatalyzed aldol reaction or Wittig based chain extension and functionalization to give enantiopure 1,5,6‐trideoxy‐1,5‐imino‐hexitols such as 10a (L‐manno) and 10b (D‐gluco). These two compounds are of interest as glycosidase inhibitors. The elaborated organocatalytic process includes diastereoselective syn aldol reaction of (S)‐isoserinal hydrate and hydroxyacetone or 1‐hydroxy‐2‐octanone and is promoted by various amino acid‐based catalysts. Diastereoselectivities of up to 8:1 were achieved, thus establishing a new, efficient synthetic route to these important carbohydrate mimics.
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