Amino alcohols are found in a wide variety of biologically active compounds and have been used as chiral ligands for transition metal catalysts and to induce chirality. In order to investigate the properties of 3-amino alcohols, an efficient synthetic route to both enantiomers is needed. Reduction of derivatized malonate diesters with LiAlH4 yields 1,3-diols in good yields. Chemoenzymatic synthesis of chiral acyl alcohol common intermediates is achieved by allowing a Lipase to react with either a prochiral diol or a diacetate. Reaction of acyl alcohols with diphenyl phosphoroazide yields an acyl azide that is immediately reduced to give the desired 3-amino alcohol. The enantiomer of the 3-aminoalcohol is synthesized by manipulation of the protecting groups and repetition of the azidation and reduction chemistry. The synthetic route outlined above produces good yields in each step and results in synthesis of both enantiomers of 3-aminoalcohols from a common acyl alcohol intermediate.

Chemoenzymatic synthesis of both enantiomers of 3-aminoalcohols from a common intermediate

245th National Meeting (2013)

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