Tertiary Enamide-Triggered SEAr: Domino Allylation and Enamine-Type Addition

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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Bibliographic Details
Published inOrganic letters Vol. 21; no. 6; pp. 1569 - 1573
Main Authors Beltran, Frédéric, Miesch, Laurence
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.03.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PATHWAYS
CYCLOADDITION
FORMYLMETHYL-SUBSTITUTED ENAMIDES
EXPEDIENT
PYRIDINES
SPIROCYCLIZATION
DERIVATIVES
HIGHLY EFFICIENT
INTRAMOLECULAR ADDITION
CYCLIZATION
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03987