Ln(OTf)3-catalysed highly regioselective alcoholysis of 2,3-epoxy alcohols?

Organic & Biomolecular Chemistry Pub Date: 2019-03-02 DOI: 10.1039/C8OB02448K

Abstract

Regioselectivity of Ln(OTf)3-catalysed alcoholysis of 2,3- and 3,4-epoxy alcohols was closely investigated to expand the scope of the transformations. The synthetic use was demonstrated by application to the construction of 4-propoxy-5-hydroxy-2,3-pentanedione (C4-propoxy-HPD), which is a potent synthetic mediator in AI-2 quorum sensing.

Graphical abstract: Ln(OTf)3-catalysed highly regioselective alcoholysis of 2,3-epoxy alcohols
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