Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of α-Amino Acids and Derivatives
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Name Reactions
Recent Literature
A nucleophilic acid-free addition of dicyanomethyl acetate to N-methylaldimines
gives
α-(N-methyl-N-acetyl)amino acid methyl esters in
excellent yield.
H. Nemoto, T. Kawamura, N. Miyoshi, J. Am. Chem. Soc.,
2005,
127, 14546-14547.
Bis[2-(4,6-difluorophenyl)pyridinato-C2,N](picolinato)iridium(III) (FIrpic)
is an effective catalyst of a visible-light photoredox reaction of N,N-dimethylaniline
derivatives and aryl isocyanates or aryl isothiocyanates to yield α-amino amides
or α-amino thioamides. The reaction involves generation of α-aminoalkyl radicals
from tertiary amines, followed by radical addition to the electron-deficient
carbon of the isocyanates or isothiocyanates.
H. Zhou, P. Lu, X. Gu, P. Li, Org. Lett., 2013,
15, 5646-4649.
The addition of carbamoyl anions derived from N,N-disubstituted
formamides and LDA to N-tert-butyl nitrones provided a direct
route to α-(N-hydroxy)amino amides. Derivatization of the products by
tert-butyl deprotection or N-deoxygenation was demonstrated.
J. T. Reeves, C. Lorenc, K. Camara, Z. Li, H. Lee, C. A. Busacca, C. H.
Senanayake, J. Org. Chem., 2014,
79, 5895-5902.
In the presence of oxygen and a small amount of AIBN as radical initiator,
primary amines are oxidatively coupled to imines and tertiary amines are
cyanated to α-aminonitriles. These metal-free aerobic oxidative coupling
reactions may find applications in a wide range of green oxidation chemistry.
L. Liu, Z. Wang, X. Fu, C.-H. Yan, Org. Lett., 2012,
14, 5692-5695.