Categories: C-C Bond Formation > Oxygen-containing molecules, Nitrogen-containing molecules > Carbonyl compounds >

Synthesis of α-amino ketones, aldehydes and derivatives

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Recent Literature

The merger of transition metal and photoredox catalysis enables a direct enantioselective acylation of α-amino C(sp³)-H bonds with carboxylic acids to produce highly valuable α-amino ketones in high enantioselectivities under mild conditions.
X. Shu, L. Huan, Q. Huang, H. Huo, J. Am. Chem. Soc., 2020, 142, 18310-18316.

A general and convenient thiazolium-catalyzed cross-coupling of various aldehydes with acylimines derived from sulfonylamides provides ready access to structurally diverse α-amido ketones.
J. A. Murry, D. E. Frantz, A. Soheili, R. Tillyer, E. J. J. Grabowski, P. J. Reider, J. Am. Chem. Soc., 2001, 123, 9696-9697.

A coordination-assisted strategy enables a rhodium-catalyzed regio- and enantioselective addition of unfunctionalized aldehydes to internal alkenes such as enamides and β,γ-unsaturated amides. Valuable α-amino ketones and 1,4-dicarbonyl compounds were directly obtained with high enantioselectivity from readily available materials.
X. Sun, P.-C. Gao, Y.-W. Sun, B.-J. Li, J. Am. Chem. Soc., 2024, 146, 723-732.

A thiol-promoted site-specific addition of 1,3-dioxolane to imines through a radical chain process enables a metal-free and redox-neutral conversion of inexpensive materials to a broad range of protected α-amino aldehydes in very good yields using only a catalytic amount of radical precursor. Both the thiol and a small amount of oxygen from air are indispensable to the success of this reaction.
H. Zeng, S. Yang, H. Li, D. Lu, Y. Gong, J.-T. Zhu, J. Org. Chem., 2018, 83, 5256-5266.

A photocatalytic decarboxylative coupling of imine and 2,2-diethoxyacetic acid in the presence of a nonstoichiometric amount of a radical initiator provides α-aminoacetals. This atom-economical C-C coupling tolerates various functional groups. The diversely functionalized α-aminoacetals serve as a promising platform for further research.
S. Kim, B. Park, G. S. Lee, S. H. Hong, J. Org. Chem., 2023, 88, 6532-6537.

Chelated enolates are good nucleophiles for reactions with acyl halides and imidazolides affording α-amino-β-keto esters. In most cases, the reactions are over after a few minutes and preparatively useful yields are obtained, independent of the protecting groups and electrophile used. With chloroformates as acylating agents, various protected amino malonates become accessible.
K. Schultz, L. Stief, U. Kazmaier, Synthesis, 2012, 44, 600-604.