Doyle−Kirmse Reaction of Allylic Sulfides with Diazoalkane-Free (2-Furyl)carbenoid Transfer

In the presence of rhodium catalyst, (2-furyl)carbenoids generated from conjugated ene-yne-carbonyl compounds 1 efficiently undergo carbene transfer reactions with allylic sulfides followed by [2,3]sigmatropic rearrangement of sulfur ylides to give furan-containing sulfides in good yields. When dial...

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Published inOrganic letters Vol. 5; no. 15; pp. 2619 - 2621
Main Authors Kato, Yumiko, Miki, Koji, Nishino, Fumiaki, Ohe, Kouichi, Uemura, Sakae
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.07.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANOSULFUR COMPOUNDS
DI(ALLYL)
DI(PROPARGYL)
COMPLEXES
ENANTIOSELECTIVE SYNTHESES
CYCLOPROPANATION
YLIDES
TRIMETHYLSILYLDIAZOMETHANE
<2,3>-SIGMATROPIC REARRANGEMENT
CARBON CONFIGURATION
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Summary:In the presence of rhodium catalyst, (2-furyl)carbenoids generated from conjugated ene-yne-carbonyl compounds 1 efficiently undergo carbene transfer reactions with allylic sulfides followed by [2,3]sigmatropic rearrangement of sulfur ylides to give furan-containing sulfides in good yields. When diallyl sulfide is employed, heteroatom-containing polycyclic compounds are obtained by sequential intramolecular Diels−Alder cyclization reaction with a constructed furan ring as an enophile.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol034731q