Abstract
The promising performance of copper(II) complexes was demonstrated for asymmetric boron conjugate addition to α,β-unsaturated nitriles in water. The catalyst system, which consisted of Cu(OAc)2 and a chiral 2,2′-bipyridine ligand, enabled β-borylation and chiral induction in water. Subsequent protonation, which was accelerated in aqueous medium, led to high activity of this asymmetric catalysis. Both solid and liquid substrates were suitable despite being insoluble in water.
Highlights
In recent years, optically active organoboranes have attracted considerable attraction as versatile synthons for the synthesis of biologically interesting compounds and of other materials
Compounds with a nitrile group in the β-position with respect to the boron moiety represent an important subset of organoboron intermediates because these compounds contain two functional groups
The nitrile group can be transformed into a range of functional groups, such as amides [5], carboxylic acids [6], aldehydes [7], esters [8], alcohols [9], and amines [10]
Summary
Optically active organoboranes have attracted considerable attraction as versatile synthons for the synthesis of biologically interesting compounds and of other materials. Enantioselective boron conjugate addition to α,β-unsaturated nitriles provides one of the most efficient routes to chiral β-boryl nitriles. Homogeneous catalysts composed of Cu(OAc)2 were found to be more effective than insoluble Cu(OH)2-based catalysts in the asymmetric β-borylation of α,β-unsaturated nitriles in water [1,19]. We describe the Cu(II)-catalyzed asymmetric boron conjugate addition of α,β-unsaturated nitriles in water.
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