Iron-Catalyzed Doyle−Kirmse Reaction of Allyl Sulfides with (Trimethylsilyl)diazomethane

Iron salts efficiently catalyze the Doyle−Kirmse reaction of allyl sulfides with (trimethylsilyl)diazomethane and ethyl diazoacetate in dichloroethane at 83 °C. Competitive dimerization is less of a problem with (trimethylsilyl)diazomethane than with ethyl diazoacetate. Good results are obtained usi...

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Bibliographic Details
Published inOrganic letters Vol. 2; no. 9; pp. 1303 - 1305
Main Authors Carter, David S, Van Vranken, David L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.05.2000
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACETALS
TRIMETHYLSILYLDIAZOMETHANE
<2,3>-SIGMATROPIC REARRANGEMENT
COMPLEXES
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Summary:Iron salts efficiently catalyze the Doyle−Kirmse reaction of allyl sulfides with (trimethylsilyl)diazomethane and ethyl diazoacetate in dichloroethane at 83 °C. Competitive dimerization is less of a problem with (trimethylsilyl)diazomethane than with ethyl diazoacetate. Good results are obtained using only 1.5 equiv of (trimethylsilyl)diazomethane, even without slow addition. Phosphine ligands affect the kinetics, but not the diastereoselectivity. Dppe and BINAP lead to higher yields than dppp, but no enantioselection was detected with R-(+)-BINAP.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol005740r