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Methyl ketone self-condensation is a side-reaction which can be avoided through the addition of TiCl 4 [12] into the reaction mixture (to act as a water scavenger). [13] [14] An example of an aldehyde reacting with a secondary amine to form an enamine via a carbinolamine intermediate is shown below: Enamine synthesis with a carbinolamine ...
The Hajos–Parrish–Eder–Sauer–Wiechert and Barbas-List [1] reactions in organic chemistry are a family of proline-catalysed asymmetric aldol reactions.. In the 1970s, two research groups discovered (and published) almost simultaneously their discoveries of two related intramolecular reactions: Zoltan Hajos and David Parrish at Hoffmann-La Roche [2] [3] and Rudolf Wiechert et al at ...
The Stork enamine alkylation involves the addition of an enamine to a Michael acceptor (e.g., an α,β -unsaturated carbonyl compound) or another electrophilic alkylation reagent to give an alkylated iminium product, which is hydrolyzed by dilute aqueous acid to give the alkylated ketone or aldehyde. [1] Since enamines are generally produced ...
Acetoacetate decarboxylase has a K M for acetoacetate of 7×10 −3 M whereas the enzyme has a K I for benzoylacetone of 1.9×10 −6 M. [15] An enamine is most likely formed upon interaction of beta-diketones with free enzyme. The reaction of acetoacetate decarboxylase with p-chloromercuriphenylsulfonate (CMS) results in decreased catalytic ...
The aldol reaction (aldol addition) is a reaction in organic chemistry that combines two carbonyl compounds (e.g. aldehydes or ketones) to form a new β-hydroxy carbonyl compound. Its simplest form might involve the nucleophilic addition of an enolized ketone to another: These products are known as aldols, from the ald ehyde + alcoh ol, a ...
Proline organocatalysis. Proline organocatalysis is the use of proline as an organocatalyst in organic chemistry. This theme is often considered the starting point for the area of organocatalysis, even though early discoveries went unappreciated. [1] Modifications, such as MacMillan’s catalyst and Jorgensen's catalysts, proceed with excellent ...
Hantzsch pyrrole synthesis. The Hantzsch Pyrrole Synthesis, named for Arthur Rudolf Hantzsch, is the chemical reaction of β-ketoesters (1) with ammonia (or primary amines) and α-halo ketones (2) to give substituted pyrroles (3). [1][2] Pyrroles are found in a variety of natural products with biological activity, so the synthesis of ...
RXNO:0000335. 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 ...
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