A New Route from D-Mannitol to Enantiomerically Pure (S)-1-Alkylamino-3-aryloxy-2-propanols.

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Abstract
A new route to (S)-1-alkylamino-3-aryloxy-2-propanols starting from D-mannitol is described. The overall strategy involves preparation of 2,5-O-methylene-D--mannitol, tosylation of the 1,6-hydroxy groups, protection of the 3,4-hydroxy groups as a cyclic ortho ester, substitution of the tosyl groups for aryl groups, and then deprotection of the 3,4-diol system which is then cleaved by lead tetraacetate. After reduction of the resulting dialdehyde to the corresponding dialcohol, the latter is converted to the bis(methaneslfonyl) ester. Hydrolysis of the methylene acetal and substitution of the mesylate by amine yields the final compound in > 99% enantiomeric purity.