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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 Agami mechanism (1984) has an enamine intermediate with two proline units involved in the transition state (based on experimental reaction kinetics) [17] and according to a mechanism by Houk (2001) [18] [19] a single proline unit suffices with a cyclic transition state and with the proline carboxyl group involved in hydrogen bonding.
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 ...
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 ...
Acetoacetate decarboxylase (AAD or ADC) is an enzyme (EC 4.1.1.4) involved in both the ketone body production pathway in humans and other mammals, and solventogenesis in bacteria. Acetoacetate decarboxylase plays a key role in solvent production by catalyzing the decarboxylation of acetoacetate, yielding acetone and carbon dioxide. [1]
The enzyme deoxyribose-phosphate aldolase (EC 4.1.2.4) catalyzes the reversible chemical reaction. This enzyme belongs to the family of lyases, specifically the aldehyde-lyases, which cleave carbon-carbon bonds. The systematic name of this enzyme class is 2-deoxy-D-ribose-5-phosphate acetaldehyde-lyase (D-glyceraldehyde-3-phosphate-forming).
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 ...
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 substituted pyrroles has important ...