Metal triflates-catalyzed conjugate addition of homochiral Pyrroles to alpha,beta-unsaturated esters

The Friedel-Crafts reaction of homochiral pyrrole derivatives with alpha,beta-unsaturated esters catalyzed by metal triflates furnished conjugate addition products. The best yields were obtained by using yttrium triflate and methyl 4-phenyl-2-oxobut-3-enoate (2a). The addition worked regioselectivel...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 15; pp. 2574 - 2578
Main Authors Unaleroglu, C, Temelli, B, Demir, AS
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 18.10.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
homochiral pyrroles
metal triflates
INTRAMOLECULAR CARBENOID REACTIONS
ALKYLATION
KETOESTERS
pyrroles
conjugate addition
DERIVATIVES
Friedel-Crafts reaction
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Summary:The Friedel-Crafts reaction of homochiral pyrrole derivatives with alpha,beta-unsaturated esters catalyzed by metal triflates furnished conjugate addition products. The best yields were obtained by using yttrium triflate and methyl 4-phenyl-2-oxobut-3-enoate (2a). The addition worked regioselectively at C-5 of pyrrole. The diastereoisomers were separated by column chromatography.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2004-831195