There is a growing interest in boron-containing peptide and small molecule inhibitors of serine and threonine proteases (and a host of other targets). This interest drives research aimed at new methods of synthetic installation of the boroamine functional group. In the past, I mentioned some of my lab’s work in this area. My former PhD student Zhi He (now a postdoctoral fellow with Tim Jamison at MIT) and Adam Zajdlik (currently a second year PhD student in my lab) have laid a foundation for making boron-containing amines using amphoteric reagents. We are actively investigating this area and are collaborating with the lab of Ben Cravatt. We are also beginning what will hopefully be a productive collaborative relationship with Anacor in Palo Alto, CA. In July of this year Adam is going to San Francisco, where he will use his methods of boroamine synthesis in collaboration with Anacor.
I pay attention to other labs’ advances in this area and want to mention an excellent Org Lett paper by Bernard Carboni and colleagues from Rennes, France. This work describes an imaginative new way to access alpha-boryl amines using [3,3]-sigmatropic rearrangement. Below is the main idea this work is based on. Given the widespread availability of vinyl boronate building blocks, the reaction constitutes a promising new way of installing B-C-N motifs into organic molecules.