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Issue 19, 2002
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Diastereoselective [2,3]-sigmatropic rearrangements of lithium N-benzyl-O-allylhydroxylamides bearing a stereogenic centre adjacent to the migration terminus

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Abstract

The diastereoselective [2,3]-sigmatropic rearrangements of lithium N-benzyl-O-allylhydroxylamides bearing a stereogenic centre adjacent to the migration terminus are examined. (E)-N-Benzyl-O-(4-phenylpent-2-enyl)hydroxylamine rearranges in 30% de to afford syn-(3RS,4RS)-3-(N-benzyl-N-hydroxy)-4-phenylpent-1-ene as the major diastereoisomer, consistent with the rearrangement proceeding under moderate steric control. Rearrangements of both lithium (E)- and (Z)-N-benzyl-O-(4-methoxy-4-phenylbut-2-enyl)hydroxylamides furnish syn-(1RS,2RS)-1-phenyl-1-methoxy-3-(N-benzylamino)but-3-ene in ≥90% and 88% de respectively, consistent with these rearrangements proceeding under chelation control.

Graphical abstract: Diastereoselective [2,3]-sigmatropic rearrangements of lithium N-benzyl-O-allylhydroxylamides bearing a stereogenic centre adjacent to the migration terminus

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Publication details

The article was received on 18 Jul 2002, accepted on 01 Aug 2002 and first published on 02 Sep 2002


Article type: Paper
DOI: 10.1039/B207069N
Citation: J. Chem. Soc., Perkin Trans. 1, 2002,0, 2141-2150
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    Diastereoselective [2,3]-sigmatropic rearrangements of lithium N-benzyl-O-allylhydroxylamides bearing a stereogenic centre adjacent to the migration terminus

    S. D. Bull, S. G. Davies, S. H. Domíngez, S. Jones, A. J. Price, T. G. R. Sellers and A. D. Smith, J. Chem. Soc., Perkin Trans. 1, 2002, 0, 2141
    DOI: 10.1039/B207069N

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