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.
Related
An iridium-catalyzed, chemoselective, asymmetric transfer hydrogenation of α-substituted
acetophenones using formic acid as reductant can be performed in water and open
to air.
O. Soltani, M. A. Ariger, H. Vázquez-Villa, E. M. Carreira, Org. Lett., 2010,
12, 2893-2895.
(R)-β-Hydroxy nitriles were obtained via a reduction catalyzed by a
recombinant carbonyl reductase with excellent optical purity and were further
converted to (R)-β-hydroxy carboxylic acids via a nitrilase-catalyzed
hydrolysis. The present study allows ready access to both chiral β-hydroxy
nitriles and β-hydroxy carboxylic acids of pharmaceutical importance.
D. Zhu, H. Ankati, C. Mukherjee, Y. Yang, E. R. Biehl, L. Hua, Org. Lett., 2007,
9, 2561-2563.
