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  • Title: Direct catalytic addition of alkylnitriles to aldehydes by transition-metal/NHC complexes.
    Author: Sureshkumar D, Ganesh V, Kumagai N, Shibasaki M.
    Journal: Chemistry; 2014 Nov 24; 20(48):15723-6. PubMed ID: 25252112.
    Abstract:
    Direct catalytic addition of alkylnitriles to aldehydes allows for an atom-economical access to β-hydroxynitriles under proton transfer conditions. Direct use of alkylnitriles as pronucleophiles has been hampered due to their low acidity resulting in an inability to generate α-cyano carbanions in a catalytic manner. A transition metal/N-heterocyclic carbene (NHC) complex prepared from [{Rh(OMe)(cod)}2] and an imidazolium-based carbene was identified as an effective catalyst to promote the reaction with as little as 1.25 mol% of catalyst loading. The corresponding Rh complex, derived from chiral triazolium salt, rendered the reaction enantioselective, albeit with moderate enantioselectivity.
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