Alternatives to organoboron reagents in rhodium-catalyzed conjugate additions.

The rhodium-catalyzed conjugate addition of organoboron reagents to alkene acceptors has emerged as an important methodology in organic synthesis. The process results in the formation of new carbon-carbon bonds, and in principle, can create new stereocenters at both the alpha and beta carbon atoms of the acceptor. Other organometallics are known to participate in the key transmetalation to rhodium and are becoming more established in stereoselective synthesis (notably arylzinc reagents). This Focus Review will describe recent developments in the use of alternative organometallic donors to organoboron reagents in rhodium-catalyzed conjugate addition reactions and their growing applications in synthesis.