Enantiospecific and Iterative Suzuki–Miyaura Cross-Couplings

The Suzuki-Miyaura cross-coupling reaction has emerged as one of the most powerful methods for the construction of carbon-carbon bonds. Though most widely utilized for the synthesis of sp²-sp² linkages, the use of this reaction to form stereochemistry-bearing sp²-sp³ bonds has received widespread attention over the past decade. This Perspective highlights approaches to the synthesis of enantioenriched molecules via the Suzuki-Miyaura reaction. Particular focus is placed on the use of enantiomerically enriched organoboron compounds as coupling partners in stereospecific processes, as well as the development of enantioconvergent and group-selective reactions. In addition, progress in the development of chemoselective, iterative cross-coupling methods will be discussed.