Abstract
The enzymatic resolution of both syn-2-azido-1,3,4-trihydroxybutane 1 and syn-2-azido-1,4-diacetoxy-3-hydroxybutane 2 have been undertaken with different lipases as catalysts and vinyl acetate as acylating agent. Lipases Amano PS and Amano AK proved to be the superior catalysts for this resolution. Indeed, both enantiomers of 1 are easily available in good yields and very good e.e.s (up to >99%). The use of chiral HPLC with a Chiralcel OD-H column allowed the determination of e.e.s of both diacetate 2 and triacetate 3 ( syn-2-azido-1,3,4-triacetoxybutane) in a single analysis and thus facilitated the precise control of the reaction.
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