Both α- and β-aminoboronic acids and their derivatives are particularly useful as synthetic precursors, biochemical probes and drugs, although the development of novel compounds has long been hindered by the lack of synthetic options. We highlight the developments in this field, starting from the landmark Matteson homologation methodology, and moving to some elegant and convenient methods reported mainly over the last 4 years. Here, these novel and often very general methods are described and compared with each other, with their respective benefits and potential drawbacks defined. We focus on their stereoselectivity and determine whether the methods are substrate or catalyst controlled, or yield racemic mixtures.