Author(s): Anna Page
Mentor(s): Ryan E. Looper, John Kim
Institution U of U
α-Aminoboronates are essential structural motifs in many boron-containing compounds developed for medicinal use, such as bortezomib, ixazomib and delanzomib, all anti-cancer medications. While chiral α-aminoboronates are typically synthesized via the Matteson homologation, the process is technically demanding and complex, as it requires multiple steps to be done at subzero temperatures. A recent reaction developed by the Marder group involves a multicomponent coupling of various salicylaldehydes, secondary amines, and B2(OH)4 that successfully produces cyclic α-aminoboronates; however, it has yet to be demonstrated with chiral amines. Given the growing interest in incorporating chiral building blocks and a chiral tetrahedral boron center into our desired scaffold for potential new antibiotics, it is essential to develop a diastereoselective version of this reaction. This advancement would ensure precise control over the stereochemistry, which is critical for the desired biological activity and effectiveness of the antibiotics. Notably, utilizing chiral amines, such as D-Proline Methyl Ester, L-Ephedrine, and L-Proline, produces a single diastereomer with excellent yields. These results suggest that the 3-component coupling reaction may provide a novel application for producing chiral α-aminoboronates in boron-containing therapeutic compounds.