Categories: C-N Bond Formation > Amines >
Synthesis of α-Amino ketones, acids, esters, nitriles and related compounds
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Recent Literature
Use of cinchona ligands with an anthraquinone (AQN) core, in place of the
usual phthalazine (PHAL) core, in the asymmetric aminohydroxylation of
cinnamates causes dramatic reversal of the regioselection, so that phenyl
serines are obtained in high enantiomeric excess. Hence, the regioselectivity is
controlled by the ligand and not the substrate.
B. Tao, G. Schlingloff, K. B. Sharpless, Tetrahedron Lett., 1998,
39, 2507-2510.
A mild and efficient monocarboxymethylation of a broad range of primary amines
takes place under aqueous conditions at room temperature. Treatment of primary
amines with two equivalents of glyoxylic acid leads to N-formyl glycine
derivatives. Subsequent hydrolysis of the crude reaction solution gives
monocarboxymethylated products in very good yield.
T. J. K. Gibbs, M. Boomhoff, N. C. O. Tomkinson, Synlett, 2007,
1573-1575.
A highly efficient copper-catalyzed asymmetric insertion of α-diazoesters into
N-H bonds using chiral spiro bisoxazoline ligands affords α-amino acid derivatives in high yields with excellent
enantioselectivities.
B. Liu, S.-F. Zhu, W. Zhang, C. Chen, Q.-L. Zhou, J. Am. Chem. Soc., 2007,
129, 5834-5835.
D. F. Taber, R. B. Sheth, P. V. Joshi, J. Org. Chem., 2005,
70, 2851-2854.
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.
Different aldehydes and amines react with acyl cyanides in the presence of a
catalytic amount of the Schreiner thiourea catalyst to give the corresponding N-acyl amino nitriles in high yields. The scope of the reaction is broad and
allows the use of both aromatic and aliphatic aldehydes and amines.
S. C. Pan, B. List, Synlett, 2007, 318-320.
The regio- and stereoselective aminochlorination of α,β-unsaturated ketones
with N,N-dichloro-p-toluenesulfonamide (4-TsNCl2) and
CuOTf as catalyst provides an easy access to
vicinal haloamino ketones, with excellent regioselectivity and good yields.
Aromatic and aliphatic enones give opposite regioselectivity.
D. Chen, C. Timmons, S. Chao, G. Li, Eur. J. Org. Chem., 2004,
3097-3101.
L-Proline-catalyzed asymmetric α-amination of ketones proceeds with various azodicarboxylates as the
nitrogen source in high yields and excellent enantioselectivities. The scope and potential of the reaction are demonstrated by further
transformation of the α-hydrazino ketones formed to both optically active syn and
anti-α-amino alcohol derivatives.
N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Gogevig, K. A. Jorgensen, J. Am. Chem. Soc., 2002,
124, 6254-6255.
A novel enantioselective synthesis of α-amino acids has been developed,
which is broad in scope, simple in application, and advantageous for many α-amino acids
of interest in chemistry, biology, medicine.
E. J. Corey, J. O. Link, J. Am. Chem. Soc., 1992,
114, 1906-1908.
