Functionalization of Silyldienol Ethers at the γ‑Position via 2‑Silyloxypentadienyl Cations
This report describes Brønsted acid catalyzed de novo synthesis of silyldienol ethers bearing tetrasubstituted double bonds via an intermediacy of 2-silyloxypentadienyl cations. The reactivity of these novel cationic intermediates could be modulated and harnessed toward direct nucleophilic additions...
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Veröffentlicht in: | Organic letters 2016-03, Vol.18 (5), p.1084-1087 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | This report describes Brønsted acid catalyzed de novo synthesis of silyldienol ethers bearing tetrasubstituted double bonds via an intermediacy of 2-silyloxypentadienyl cations. The reactivity of these novel cationic intermediates could be modulated and harnessed toward direct nucleophilic additions regioselectively at the γ-position to produce highly functionalized silyldienol ethers with tunable control of the resulting double bond geometry. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.6b00196 |