Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of β-Cyanohydrins
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Recent Literature
Cooperative catalysis of a cationic Ru complex, DBU, and NaPF6 enabled
activation of acetonitrile as a nucleophile under mild basic conditions. The
nucleophilic 1,2-addition of in situ-generated, Ru-bound, metalated nitrile to
aldehydes and imines proceeded smoothly.
N. Kumagai, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc.,
2004,
126, 13632-13633.
In the presence of SiCl4 and a catalytic amount of a chiral
phosphoramide, silyl ketene imines undergo extremely rapid and high yielding
addition to a wide variety of aromatic aldehydes with excellent diastereo- and
enantioselectivity. The nitrile function serves as a useful precursor for
further synthetic manipulation.
S. E. Denmark, T. W. Wilson, M. T. Burk, J. R. Heemstra, Jr., J. Am. Chem. Soc., 2007,
129, 14864-14865.
