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α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

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Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
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Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

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Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
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α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Accessing α-Ketoamides on DNA through a Coupling-Oxidation Strategy.

Xianfu Fang1,2, Xin Wang2, Qigui Nie2,3

  • 1Pharmaceutical Department, Chongqing University Three Gorges Hospital, Chongqing University, Chongqing 404100, China.

Organic Letters
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Researchers developed a novel on-DNA synthesis strategy to create α-ketoamides, crucial for drug discovery. This method expands DNA-encoded libraries (DELs) by enabling efficient synthesis of diverse α-ketoamide compounds.

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Area of Science:

  • Medicinal Chemistry
  • Synthetic Chemistry
  • Biotechnology

Background:

  • α-Ketoamides are vital pharmacophores in drug discovery.
  • Their incorporation into DNA-encoded libraries (DELs) is limited by a lack of efficient on-DNA synthetic methods.

Purpose of the Study:

  • To develop a robust on-DNA synthetic strategy for α-ketoamide precursors.
  • To expand the chemical diversity accessible within DNA-encoded libraries.

Main Methods:

  • An on-DNA coupling-oxidation strategy was employed to synthesize DNA-conjugated α-hydroxyamides.
  • Subsequent oxidation converted α-hydroxyamides into α-ketoamides.

Main Results:

  • The protocol demonstrated broad substrate scope and excellent functional group tolerance, especially for mandelic acid derivatives.
  • It enabled the collective transformation of α-hydroxyamide libraries into α-ketoamide libraries.
  • This significantly increased the chemical space accessible for DELs.

Conclusions:

  • A novel and efficient on-DNA synthetic route to α-ketoamides has been established.
  • This method overcomes previous limitations, enabling broader application of DELs in drug discovery.
  • The strategy facilitates the generation of diverse α-ketoamide libraries for screening.