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.
Direct electrocarboxylation of various N-acylimines with atmospheric
CO2 is achieved in an undivided cell under mild conditions, affording
substituted α-amino acids in good yields. The reaction can be conducted with
high efficiency using triethanolamine as an external reductant under
nonsacrificial anode conditions.
K. Zhang, X.-F. Liu, W.-Z. Zhang, W.-M. Ren, X.-B. Lu, Org. Lett.,
2022, 24, 3566-3569.
Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as
precursors to carbamoyl radicals that undergo rapid addition to N-aryl
imines. This operationally simple reaction proceeds under blue light irradiation
in the presence of the photocatalyst 3DPAFIPN and Brønsted/Lewis acid additives.
L. Cardinale, M.-O. W. S. Schmotz, M. O. Konev, A. J. von Wangelin, Org. Lett., 2022, 24,
506-510.
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.
A diastereoselective addition of carbamoyl anions to azirines affords
synthetically useful 2-aziridinyl amide building blocks. A one-pot conversion of
a ketoxime to an aziridinyl amide was also demonstrated.
M. J. Kerner, C. A. Kuttruff, M. Chevliakov, F. G. Buono, D. A. Gao, M.
Krawiec, C. A. Busacca, C. H. Senanayake, P. Wipf, J. T. Reeves, Org. Lett., 2021, 23,
4396-4399.