Synthesis of octitols and the respective amino-derivatives from 'organo-aldols'

Abstract

Two diastereoisomeric keto-octoses, obtained in the reaction of 2,3:4,5-diacetone-D-arabinose with protected dihydroxyacetone catalyzed with L- or D-proline, were converted into octitols by stereoselective reduction of the carbonyl group with zinc borohydride and final deprotection. The study on the preparation of the respective amino-derivatives by reductive amination of these organo-adducts is presented; stereochemical aspects of these processes are discussed.

Keywords: Amino-octitols; Octitols; Organocatalysis; Stereoselective synthesis.