Synthesis of β-substituted β-aminoboronates

Abstract

Recent work at the University of Tromsø has uncovered new α-substituted α- and β-aminoboron containing peptidomimetics that shows antimicrobial, antifungal and antitubercular activity in addition to kinase inhibition and promotion.

As a continuation of this work a new approach for the synthesis of β-substituted β-aminoboronates has been developed.

The approach involves the non-stereospecific synthesis of β-substituted β-aminoboronates followed by oxidation to the boronic acid and subsequent esterification using an enantiomerically pure carbohydrate in order to increase water solubility and potential activity.

The oxidation to the boronic acid and following esterification has not yet been accomplished for the target molecules, but exploratory reactions seem to indicate that it is possible.

It was also discovered that for certain benzylic halides ultrasound quite unexpectedly led to dimerisation. The scope and limitations of this discovery was explored.