Synthesis of oxetane and azetidine ethers as ester isosteres by Brønsted acid catalysed alkylation of alcohols with 3-aryl-oxetanols and 3-aryl-azetidinols
Oxetanes and azetidines continue to draw significant interest in medicinal chemistry, as small, polar and non-planar motifs. Oxetanes also represent interesting surrogates for carbonyl-containing functional groups. Here we report a synthesis of 3,3-disubstituted oxetane- and azetidine-ethers, with comparisons made to the ester functional group. The tertiary benzylic alcohols of the 4-membered rings are selectively activated using Brønsted acid catalysis and reacted with simple alcohols to form the ethers and maintain the oxetane ring intact. This approach avoids the use of strong bases and halide alkylating agents and allows alcohol libraries to be leveraged. Oxetane ethers demonstrate excellent chemical stability across a range of conditions and an improved stability vis-à-vis analogous esters under basic and reducing conditions.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:21 |
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| Enthalten in: |
Organic & biomolecular chemistry - 21(2023), 27 vom: 12. Juli, Seite 5553-5559 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Saejong, Peerawat [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 12.07.2023 Date Revised 18.07.2023 published: Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1039/d3ob00731f |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM35846899X |
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| 100 | 1 | |a Saejong, Peerawat |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis of oxetane and azetidine ethers as ester isosteres by Brønsted acid catalysed alkylation of alcohols with 3-aryl-oxetanols and 3-aryl-azetidinols |
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| 500 | |a Date Revised 18.07.2023 | ||
| 500 | |a published: Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a Oxetanes and azetidines continue to draw significant interest in medicinal chemistry, as small, polar and non-planar motifs. Oxetanes also represent interesting surrogates for carbonyl-containing functional groups. Here we report a synthesis of 3,3-disubstituted oxetane- and azetidine-ethers, with comparisons made to the ester functional group. The tertiary benzylic alcohols of the 4-membered rings are selectively activated using Brønsted acid catalysis and reacted with simple alcohols to form the ethers and maintain the oxetane ring intact. This approach avoids the use of strong bases and halide alkylating agents and allows alcohol libraries to be leveraged. Oxetane ethers demonstrate excellent chemical stability across a range of conditions and an improved stability vis-à-vis analogous esters under basic and reducing conditions | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Rojas, Juan J |e verfasserin |4 aut | |
| 700 | 1 | |a Denis, Camille |e verfasserin |4 aut | |
| 700 | 1 | |a White, Andrew J P |e verfasserin |4 aut | |
| 700 | 1 | |a Voisin-Chiret, Anne Sophie |e verfasserin |4 aut | |
| 700 | 1 | |a Choi, Chulho |e verfasserin |4 aut | |
| 700 | 1 | |a Bull, James A |e verfasserin |4 aut | |
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