Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of Imines
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Recent Literature
A highly regio- and enantioselective copper-catalyzed three-component coupling
of isocyanides, hydrosilanes, and γ,γ-disubstituted allylic phosphates/chlorides
provides chiral α-quaternary formimides in the presence of a chiral
naphthol-carbene ligand and LiOtBu as base. The formimides can readily be
converted to α-quaternary aldehydes.
K. Hojoh, H. Ohmiya, M. Sawamura, J. Am. Chem. Soc., 2017,
139, 2184-2187.
A palladium-catalyzed double isocyanide insertion and elimination enables an
efficient one-pot synthesis of α-iminonitriles from readily available aryl
halides without using hypertoxic cyanides and excess oxidants. Furthermore, the
utility of this reaction was demonstrated by a rapid total synthesis of a
quinoxaline.
Z.-B. Chen, Y. Zhang, Q. Yuan, F.-L. Zhang, Y.-M. Zhu, J.-K. Shen, J. Org. Chem.,
2016,
81, 1610-1616.
The direct conversion of amides, including sensitive N-vinyl amides,
to the corresponding trimethylsilyl alkynyl imines followed by a
ruthenium-catalyzed protodesilylation and cycloisomerization gives various
substituted pyridines and quinolines.
M. Movassaghi, M. D. Hill, J. Am. Chem. Soc.,
2006,
128, 4592-4593.
A 1,4-dipolar intermediate generated from pyridine and dimethyl
acetylenedicarboxylate reacted with aldehydes to give 2-benzoylfumarates via
the elimination of pyridine, whereas with N-tosylimines as
dipolarophiles the reaction afforded highly substituted 1-azadienes.
V. Nair, A. R. Sreekanth, N. Abhilash, A. T. Biju, B. R. Devi, R. S. Menon,
N. P. Rath, R. Srinivas, Synthesis,
2003, 1895-1902.