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Updated: Feb 12, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

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ダイアステロエーマー解像度によるエナチオピュアナフトジオキサンベースのカルボキシル酸およびエステル:絶対的構成割り当て

Alessia Lanzini1, Martina Pila1, Cristina Sala1

  • 1Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Milan, Italy.

Chirality
|February 11, 2026
PubMed
まとめ

この研究は,キラル補助器を用いて,エナティオメリックに純粋なナフトジオキサン誘導体を生成するための効率的な方法を示しています. 合成された化合物は,様々な変換を通じて高いエナチオ純度を保ち,薬剤設計のための貴重な中間物質を提供します.

キーワード:
(S) -フェニルエチラミン1,4‐ナフトジオキサン‐2‐アセタミド1,4‐ナフトジオキサン‐2‐カルボキシアミド1H-NMRの比較結果絶対的な構成決定の決定キラルHPLCによるHPLCディアステロエーマーアミド

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Esters to Carboxylic Acids: Saponification

Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution reaction in which esters react with an aqueous base, followed by an acid to give carboxylic acids. This reaction is also known as saponification because it forms the basis for making soaps from fats.
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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...
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The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
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The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
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The fragmentation patterns observed for compounds such as carboxylic acids, esters, and amides in the mass spectra include ⍺-cleavage and McLafferty rearrangement. Fragmentation by ⍺-cleavage preferentially occurs at the carbon-carbon bond at the ⍺-position next to the carboxylic group to generate a neutral radical and a cation. Long chain compounds with hydrogen at their γ-carbon undergo McLafferty rearrangement to give a radical cation and a neutral alkene.
For example, the...
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