α-Boryl Organometallic Reagents in Catalytic Asymmetric Synthesis

Recent years have witnessed an increase in the popularity of a-boryl organometallic reagents as versatile nucleophiles in asymmetric synthesis. These compounds have been adopted in chemo- and stereoselective coupling reactions with a number of different electrophiles. The resulting enantioenriched boronic esters can be applied in stereospecific carbon-carbon or carbon- heteroatom bond construction reactions, enabling a two-step strategy for the construction of complex structures with high efficiency and functional group compatibility. For these reasons, tremendous effort has been devoted to the preparation of enantiomerically enriched alpha-boryl organometallic reagents and to the development of stereoselective reactions of related racemic or prochiral materials. In this review, we describe enantio- or diastereoselective reactions that involve alpha-boryl organometallic reagents as starting materials or products and showcase their synthetic utility.

Automated summary

In recent years, a-boryl organometallic reagents have become popular as versatile nucleophiles in asymmetric synthesis, enabling chemo- and stereoselective coupling reactions to produce enantioenriched boronic esters. This allows for efficient construction of complex structures with high functional group compatibility. Efforts have been focused on preparing enantiomerically enriched a-boryl organometallic reagents and developing stereoselective reactions of related racemic materials.