ArticleChemistry (Weinheim an der Bergstrasse, Germany)2018
Lithium-Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3-Sulfanyl-Oxetanes as Bioisosteres.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 61 citations in OpenAlex.
- Iron-Catalyzed Friedel-Crafts Reactions of Unactivated 3-Aryl-Oxetanols Exploiting HFIP Stabilization of Carbocations.The Journal of organic chemistry · 2026Article
- Do Amino-Oxetanes Resemble Amides? A Matched Molecular Pairs Property and Structural Comparison.Journal of medicinal chemistry · 2026Article
- Synthesis ofThe Journal of organic chemistry · 2025Article
- Functionalization of Electron-Rich Secondary Benzyl Alcohols in HFIP: From Thioethers to Trisubstituted Methanes.The Journal of organic chemistry · 2025Article
- A practical one-pot synthesis of dehydroalanine esters.RSC advances · 2025Article
- Oxetanes: formation, reactivity and total syntheses of natural products.Beilstein journal of organic chemistry · 2025Review
- Harnessing Oxetane and Azetidine Sulfonyl Fluorides for Opportunities in Drug Discovery.Journal of the American Chemical Society · 2024Article
- Synthesis of 3,3-Disubstituted Thietane Dioxides.The Journal of organic chemistry · 2024Article
- Oxetanes in Drug Discovery Campaigns.Journal of medicinal chemistry · 2023Review
- Visible Light Photoredox-Catalyzed Decarboxylative Alkylation of 3-Aryl-Oxetanes and Azetidines via Benzylic Tertiary Radicals and Implications of Benzylic Radical Stability.The Journal of organic chemistry · 2023Article
- Oxetan-3-ols as 1,2-bis-Electrophiles in a Brønsted-Acid-Catalyzed Synthesis of 1,4-Dioxanes.Organic letters · 2022Article
- Amino-oxetanes as amide isosteres by an alternative defluorosulfonylative coupling of sulfonyl fluorides.Nature chemistry · 2022Article
- Benzyl thioether formation merging copper catalysis.RSC advances · 2021Article
- Investigating 3,3-diaryloxetanes as potential bioisosteres through matched molecular pair analysis.RSC medicinal chemistry · 2021Article
- From Propargylic Alcohols to Substituted Thiochromenes:The Journal of organic chemistry · 2021Article
- Put a ring on it: application of small aliphatic rings in medicinal chemistry.RSC medicinal chemistry · 2021Review
- B(CRSC advances · 2018Article
- Lithium-Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3-Sulfanyl-Oxetanes as Bioisosteres.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
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Authors and funding
4 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
3-Sulfanyl-oxetanes are presented as promising novel bioisosteric replacements for thioesters or benzyl sulfides. From oxetan-3-ols, a mild and inexpensive Li catalyst enables chemoselective C-OH activation and thiol alkylation. Oxetane sulfides are formed from various thiols providing novel motifs in new chemical space and specifically as bioisosteres for thioesters due to their similar shape and electronic properties. Under the same conditions, various π-activated secondary and tertiary alcohols are also successful. Derivatization of the oxetane sulfide linker provides further novel oxetane classes and building blocks. Comparisons of key physicochemical properties of the oxetane compounds to selected carbonyl and methylene analogues indicate that these motifs are suitable for incorporation into drug discovery efforts.
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