Homologous Mukaiyama Reactions via Trapping of the Nazarov Intermediate with Silyloxyalkenes
Treatment of 1,4-pentadien-3-ones and silyloxyalkenes with BF3·OEt2 at room temperature or lower initiates a domino process consisting of sequential 4π electrocyclization and capture of the resulting cyclopentenyl cation by the electron-rich trap. The overall process furnishes 1,4-dicarbonyl product...
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| Published in: | Organic letters Vol. 13; no. 14; pp. 3584 - 3587 |
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| Main Authors: | , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
United States
American Chemical Society
15-07-2011
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| Online Access: | Get full text |
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| Summary: | Treatment of 1,4-pentadien-3-ones and silyloxyalkenes with BF3·OEt2 at room temperature or lower initiates a domino process consisting of sequential 4π electrocyclization and capture of the resulting cyclopentenyl cation by the electron-rich trap. The overall process furnishes 1,4-dicarbonyl products containing highly substituted cyclopentanones in good yields and with the establishment of up to five new stereocenters. |
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| Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/ol201125h |