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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Name Reactions
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 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.
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.
