Tertiary Enamide-Triggered S E Ar

Tertiary Enamide-Triggered S E Ar

Two unprecedented domino reactions are described, starting from ketospiro-enesulfonamides. By treatment with ZrCl4 and allylsilane, an intramolecular electrophilic aromatic substitution and subsequent allylation is observed. By treatment with TiCl4 and allylsilane, a double enamine-type reaction tak...

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Veröffentlicht in:Organic letters 2019-03, Vol.21 (6), p.1569-1573
Hauptverfasser: Beltran, Frederic, Miesch, Laurence
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
Organic chemistry
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Zusammenfassung:Two unprecedented domino reactions are described, starting from ketospiro-enesulfonamides. By treatment with ZrCl4 and allylsilane, an intramolecular electrophilic aromatic substitution and subsequent allylation is observed. By treatment with TiCl4 and allylsilane, a double enamine-type reaction takes place, thus creating simultaneously four contiguous stereogenic centers diastereoselectively.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03987