1,2-Migration of the thio group in allenyl sulfides: Efficient synthesis of 3-thio-substituted furans and pyrroles

Angewandte Chemie - International Edition

Volumn 42, Issue 1, 2003, Pages 98-101

  Kim, Joseph T ^a   Kel'In, Alexander V ^a   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

Cyclization; Heterocycles; Homogeneous catalysis; Nitrogen heterocycles; Sulfur

Indexed keywords

CYCLOISOMERIZATION;

CATALYSTS; COPPER; ISOMERIZATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AROMATIC HYDROCARBONS;

ALLENYL SULFIDE; COPPER; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; IMINE; KETONE DERIVATIVE; N,N DIMETHYLACETAMIDE; PYRROLE DERIVATIVE; SULFIDE; SULFUR; THIOL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; ISOMERISM; REACTION ANALYSIS; SYNTHESIS;

CATALYSIS; COPPER; CYCLIZATION; FURANS; MOLECULAR STRUCTURE; NITROGEN; PYRROLES; SULFHYDRYL COMPOUNDS; SULFIDES;

EID: 0037414928     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390064     Document Type: Article

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15. 4, 2 g), and concentrated under reduced pressure. The residue was purified by means of silica-gel chromatography with hexanes to give furan 8d (187 mg. 76%).
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21. It was found that EB protecting group can very easily be removed from the pyrroles. Thus, thio-substituted pyrrole 8m underwent a facile retro-Michael reaction in the presence of KOtBu to give the corresponding pyrrole 8p quantitatively.