Abstract
Organoboron compounds are extremely useful building blocks for organic synthesis; however, they suffer from incompatibilities with many synthetic transformations, and thus are typically introduced just before their utilization. This article aims to briefly highlight the utility of the N-methyliminodiacetate (MIDA) boronate complex as a protecting group for organoboron compounds and detail the expanding role of protected organoboron compounds from merely early stage reactants to late stage complex building blocks. Mancilla and Contreras first described boron MIDA complexes in 1986; however, it is only recently that Burke and coworkers have expounded the stabilizing/deactivating properties of this functionality. This boron protecting group has subsequently been applied in the synthesis of several highly functionalized boron-containing intermediates en-route to several natural products.
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