非対称なリン酸触媒による4組分Ugi反応
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The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
Figure 1. The acid-catalyzed aldol addition reaction of ketones.
First, as shown in Figure 2, the acid protonates the ketone molecule to form the protonated ketone. The conjugate base of the acid deprotonates the α carbon of the protonated ketone to form the enol.
Figure 2. Formation of the enol.
An acid-base reaction is one in which a hydrogen ion, H+, is transferred from one chemical species to another. Such reactions are of central importance to numerous natural and technological processes, ranging from the chemical transformations within cells or lakes and oceans to the industrial-scale production of fertilizers, pharmaceuticals, and other substances essential to the society.
There are several ways of defining an acid. In the context of aqueous solutions, an acid is a substance...
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
Figure 1: The base-catalyzed aldol addition reaction of aldehydes.
The reaction preferentially occurs with simple aldehydes, where the α carbon is monosubstituted. The equilibrium of the reaction involving disubstituted aldehydes and ketones shifts backward to the reactants due to the steric interactions at the α carbon. The...
Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.
Strong acids, such as sulfuric acid, dissociate completely in an aqueous solution, and the acid participating in the reaction is the hydronium ion.
The first step is the slow protonation of an alkene at the less-substituted end to form...
Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...

