ArticleNature communications2019
Catalytic asymmetric acetalization of carboxylic acids for access to chiral phthalidyl ester prodrugs.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 63 citations in OpenAlex.
- Article
- A membrane-modulated chemoenzymatic dynamic kinetic resolution for the synthesis of chiral phthalidyl esters.Nature communications · 2026Article
- Review
- Dimethyl(alkyl) sulfates as Lewis acid type catalysts for acetalization and related reactions of carbonyl compounds.RSC advances · 2025Article
- Recent advances in synthetic approaches for bioactive cinnamic acid derivatives.Beilstein journal of organic chemistry · 2025Review
- Carbene-Catalyzed Phthalide Ether Functionalization for Discovering Chiral Phytovirucide that Specifically Targets Viral Nia Protein to Inhibit Proliferation.Research (Washington, D.C.) · 2025Article
- Tunable Thiazolium Carbenes for Enantioselective Radical Three-Component Dicarbofunctionalizations.Journal of the American Chemical Society · 2024Article
- α-Phenylthioaldehydes for the effective generation of acyl azolium and azolium enolate intermediates.Chemical science · 2024Article
- Article
- Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles.Nature communications · 2023Article
- Oxidative N-Heterocyclic Carbene Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Review
- Electroredox carbene organocatalysis with iodide as promoter.Nature communications · 2022Article
- Carbene-catalyzed enantioselective annulation of dinucleophilic hydrazones and bromoenals for access to aryl-dihydropyridazinones and related drugs.Chemical science · 2021Article
- Tale of the Breslow intermediate, a central player in N-heterocyclic carbene organocatalysis: then and now.Chemical science · 2021Review
- NHC-catalyzed covalent activation of heteroatoms for enantioselective reactions.Chemical science · 2021Review
Corrections and comments
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Authors and funding
11 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Carboxylic acids are common moieties in medicines. They can be converted to phthalidyl esters as prodrugs. Unfortunately, phthalidyl esters are now mostly prepared in racemic forms. This is not desirable because the two enantiomers of phthalidyl esters likely have different pharmacological effects. Here we address the synthetic challenges in enantioselective modification of carboxylic acids via asymmetric acetalizations. The key reaction step involves asymmetric addition of a carboxylic acid to the catalyst-bound intermediate. This addition step enantioselectively constructs a chiral acetal unit that lead to optically enriched phthalidyl esters. A broad range of carboxylic acids react effectively under mild and transition metal-free conditions. Preliminary bioactivity studies show that the two enantiomers of chlorambucil phthalidyl esters exhibit different anti-cancer activities to inhibit the growth of Hela cells. Our catalytic strategy of asymmetric acetalizations of carboxylic acids shall benefit future development of chiral phthalidyl ester prodrugs and related molecules.
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