Remote C-H insertion of vinyl cations leading to cyclopentenones
We report a Lewis acid catalyzed reaction sequence involving a 1,2-shift and subsequent C-H insertion that gives monocyclic and fused bicyclic cyclopentenone products. This reaction sequence, which is initiated by treating β-hydroxy-α-diazo ketones with a Lewis acid, proceeds through vinyl cation in...
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Veröffentlicht in: | Chemical science (Cambridge) 2017-10, Vol.8 (10), p.6810-6814 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | We report a Lewis acid catalyzed reaction sequence involving a 1,2-shift and subsequent C-H insertion that gives monocyclic and fused bicyclic cyclopentenone products. This reaction sequence, which is initiated by treating β-hydroxy-α-diazo ketones with a Lewis acid, proceeds through vinyl cation intermediates that insert at non-activated gamma C-H bonds. This reaction represents an alternative strategy to exploit the diazo functional group in an intramolecular C-H insertion, and can provide products not accessible by transition metal catalyzed C-H insertions. This remote C-H activation process provides good yields of bicyclic cyclopentenone products that contain 7- and 8-membered rings, and monocyclic prostaglandin analogs. |
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ISSN: | 2041-6520 2041-6539 |
DOI: | 10.1039/c7sc02768k |