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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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Article information


Submitted
18 Jul 2002
Accepted
01 Aug 2002
First published
02 Sep 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2141-2150
Article type
Paper

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, 2141
DOI: 10.1039/B207069N

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