Diastereoselective construction of spirocyclic isobenzofurans via a tandem Michael addition/5-exo-dig cyclization reaction
A practical approach for rapid and efficient access to spirocyclic isobenzofurans is described. The reaction proceeds through the cycloaddition of 1,6-ynenone derivatives and 4-nitro-1,3-diarylbutan-1-ones, promoted by Cs2CO3 in the presence of l-proline as a catalyst. The advantages of this reactio...
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| Main Authors: | , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
October 31, 2024
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| In: |
The journal of organic chemistry
Year: 2024, Volume: 89, Issue: 22, Pages: 16613-16621 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.4c01890 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.4c01890
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| Author Notes: | Shaghayegh Mehdidoust, Saideh Rajai-Daryasarei, S. Sina Hosseini, Frank Rominger, Hamid Reza Bijanzadeh, Saeed Balalaie, and Sorour Ramezanpour |
| Summary: | A practical approach for rapid and efficient access to spirocyclic isobenzofurans is described. The reaction proceeds through the cycloaddition of 1,6-ynenone derivatives and 4-nitro-1,3-diarylbutan-1-ones, promoted by Cs2CO3 in the presence of l-proline as a catalyst. The advantages of this reaction include the formation of two C-C bonds and one C-O bond as well as mild reaction conditions. Extended spirocyclic isobenzofurans are obtained with good efficiency and diastereoselectivity under these mild conditions, and this new protocol avoids the use of any transition-metal reagents. |
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| Item Description: | Gesehen am 15.04.2025 |
| Physical Description: | Online Resource |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.4c01890 |