Abstract
Recent advances in stereospecific and stereoselective Suzuki–Miyaura cross-coupling reactions generating chiral, enantiomerically enriched products are described. In terms of enantioenriched nucleophiles, at the present time, substrates which are effectively coupled in a stereospecific manner are limited to those with C–B bonds that are π-activated (i.e. benzylic, allylic or propargylic), in close proximity to carbonyl compounds, or have a geminal boron substituent. Prior to the work described in this highlight, the Suzuki–Miyaura cross-coupling of chiral organoboron species was limited to cyclopropyl systems. Stereoselective cross-couplings employing enantiopure secondary electrophiles are also rapidly advancing and the use of chiral, racemic electrophiles in conjunction with chiral ligands is an emerging powerful route for the creation of stereochemistry via Suzuki–Miyaura cross coupling. Advances in this area are presented in the second half of this chapter.
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