β‐Functionalized and α,β‐Difunctionalized Ketones from 1‐Arylallylic Alcohols via Dipotassio α,β‐Dianion Intermediates
This study reports the synthesis of diverse β‐functionalized ketones from readily available 1‐arylallylic alcohols in the presence of (trimethylsilyl)methylpotassium (TMSCH2K). The reaction proceeded via the formation of the highly nucleophilic dipotassio α,β‐dianion as the key intermediate, which s...
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Veröffentlicht in: | Advanced synthesis & catalysis 2023-03, Vol.365 (6), p.826-833 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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Zusammenfassung: | This study reports the synthesis of diverse β‐functionalized ketones from readily available 1‐arylallylic alcohols in the presence of (trimethylsilyl)methylpotassium (TMSCH2K). The reaction proceeded via the formation of the highly nucleophilic dipotassio α,β‐dianion as the key intermediate, which served as a metal homoenolate equivalent. This protocol also allowed the one‐pot synthesis of α,β‐difunctionalized ketones using two different electrophiles, thus demonstrating its synthetic advantages over other protocols involving metal homoenolates. |
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ISSN: | 1615-4150 1615-4169 |
DOI: | 10.1002/adsc.202201047 |