Reductive amination (also known as reductive alkylation) is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is a common method to make amines and is widely used in green chemistry since it can be done catalytically in one-pot under mild conditions. In biochemistry, dehydrogenase enzymes use reductive amination to produce the amino acid, glutamate. Additionally, there is ongoing research on alternative synthesis mechanisms with various metal catalysts which allow the reaction to be less energy taxing, and require milder reaction conditions. Investigation into biocatalysts, such as imine reductases, have allowed for higher selectivity in the reduction of chiral amines which is an important factor in pharmaceutical synthesis.[1]
^Thorpe, Thomas W.; Marshall, James R.; Harawa, Vanessa; Ruscoe, Rebecca E.; Cuetos, Anibal; Finnigan, James D.; Angelastro, Antonio; Heath, Rachel S.; Parmeggiani, Fabio; Charnock, Simon J.; Howard, Roger M.; Kumar, Rajesh; Daniels, David S. B.; Grogan, Gideon; Turner, Nicholas J. (7 April 2022). "Multifunctional biocatalyst for conjugate reduction and reductive amination". Nature. 604 (7904): 86–91. Bibcode:2022Natur.604...86T. doi:10.1038/s41586-022-04458-x. hdl:11311/1232494. ISSN 0028-0836. PMID 35388195. S2CID 248001189.
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Reductiveamination (also known as reductive alkylation) is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate...
aminases. Amination can occur in a number of ways including reaction with ammonia or another amine such as an alkylation, reductiveamination and the Mannich...
discovered that catalyzed both steps of reductiveamination of a wide scope of ketone-amine pairs. These are dubbed reductive aminases (RedAms). Engineered RedAms...
by hydrogens (hydrogenolysis). Ammonium formate can be used for reductiveamination of aldehydes and ketones (Leuckart reaction), by the following reaction:...
reduces aldehydes but not most ketones. It is especially suitable for reductiveaminations of aldehydes and ketones. However, unlike sodium cyanoborohydride...
HOR' In addition to their reduction to alcohols, aldehydes and ketones can be converted to amines, i.e., reductiveamination. Because of its cyano substituent...
chemical reaction that converts aldehydes or ketones to amines by reductiveamination in the presence of heat. The reaction, named after Rudolf Leuckart...
for the reduction of these same groups on the laboratory scale. Many amines are produced from aldehydes and ketones via reductiveamination, which can...
generally used for the reduction of imines. These reactions occur <pH 7 because the iminium ions are the actual substrates. Reductiveamination, sometimes called...
Industrially neotame is made from 3,3-dimethylbutanal and aspartame via reductiveamination. They are dissolved in methanol, palladium on carbon catalyst is...
chloride and ammonia. It is also produced by the reduction of benzonitrile and reductiveamination of benzaldehyde, both done over Raney nickel. It was...
such as valine, leucine, and isoleucine. Alanine is produced by reductiveamination of pyruvate, a two-step process. In the first step, α-ketoglutarate...
be prepared starting from phenylacetone by either the Leuckart or reductiveamination methods. In the Leuckart reaction, one equivalent of phenylacetone...
activation chemistries include cyanogen bromide (CNBr) activation and reductiveamination of aldehydes to attach proteins to the agarose resin through lysine...
antiozonants based around p-phenylenediamine. 6PPD is prepared by reductiveamination of methyl isobutyl ketone (which has six carbon atoms, hence the...
these three amines are produced industrially. It is also produced by reductiveamination of acetaldehyde. CH3CHO + NH3 + H2 → CH3CH2NH2 + H2O Ethylamine can...
Suzuki coupling, followed by a Buchwald–Hartwig amination with the final step being a reductiveamination using the Leuckart reaction. "Verzenio (Eli Lilly...
Furfurylamine is an aromatic amine typically formed by the reductiveamination of furfural with ammonia. The pharmaceutical drug furtrethonium, a parasympathomimetic...
organic synthesis. Examples include reductiveamination, carbonyl reduction, nitro compound reduction, the reduction of imines and Schiff bases and debenzylation...
Diisopropylamine, which is commercially available, may be prepared by the reductiveamination of acetone with ammonia using a modified copper oxide, generally...
via ammonolysis of acetylacetone under conditions commonly used in reductiveamination. It can also be made from anhydrous acetic acid, acetonitrile and...
palladium catalyst. Once the MDP2P intermediate has been prepared, a reductiveamination leads to racemic MDMA (an equal parts mixture of (R)-MDMA and (S)-MDMA)...
(1996). "ReductiveAmination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect ReductiveAmination Procedures"...
manufactures methamphetamine using phenylacetone and methylamine through a reductiveamination reaction. White produced phenylacetone in a tube furnace using phenylacetic...
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