Categories: C-N Bond Formation > Amines >
Synthesis of 1,1-diamines (aminals)
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VAPOL metal phosphates are superior catalysts for imine amidation reactions
to produce chiral N,N'-aminal products in high yields and with excellent
ee values. Upon optimization, a wide substrate scope, low catalyst loading, and
mild conditions are achieved.
R. Cao, J. C. Antilla,
Org. Lett., 2020, 22, 5958-5962.
C-Acylimines undergo intermolecular amidation with amides to produce monoacyl
gem-diamino acid derivatives in the presence of Cu(OTf)2 and PPh3
under mild conditions. This method provides an efficient access to gem-diamino
acid equivalents with good to excellent yields.
S. Zhu, J. Dong, S. Fu, H. Jiang, W. Zeng, Org. Lett., 2011,
13, 4914-4917.
Chelated amino acid ester enolates react with aromatic nitro compounds in a
1,3-addition mode at the nitro group giving amino acids bearing an
aryl(hydroxy)amino side chain. Two equivalents of enolate are necessary for
complete conversion, because one equivalent is oxidized during the reaction.
D. Stolz, U. Kazmaier, R. Pick,
Synthesis, 2006, 3341-3347.