Ketonitrones via Cope-Type Hydroamination of Allenes

The synthesis of ketonitrones from N-alkylhydroxylamines and monosubstituted allenes is accomplished via a Cope-type hydroamination reaction in moderate to good yields. Allenes also undergo a similar reaction with aqueous hydroxylamine to give oximes in excellent yield. DFT calculations support a pr...

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Bibliographic Details
Published inOrganic letters Vol. 11; no. 9; pp. 1895 - 1898
Main Authors Moran, Joseph, Pfeiffer, Jennifer Y, Gorelsky, Serge I, Beauchemin, André M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.05.2009
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALKENES
HYDROXYLAMINES
1,3-DIPOLAR CYCLOADDITIONS
ENANTIOSELECTIVE INTRAMOLECULAR HYDROAMINATION
NITRONES
CONVERSION
INTERMOLECULAR HYDROAMINATION
INFORMATION
ASYMMETRIC HYDROAMINATION
ELIMINATION
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Summary:The synthesis of ketonitrones from N-alkylhydroxylamines and monosubstituted allenes is accomplished via a Cope-type hydroamination reaction in moderate to good yields. Allenes also undergo a similar reaction with aqueous hydroxylamine to give oximes in excellent yield. DFT calculations support a proposed concerted, five-membered hydroamination process, and calculated transition state energies are in excellent agreement with experimental observations.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol900292r