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Synlett 2001; 2001(10): 1587-1589
DOI: 10.1055/s-2001-17444
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On the Characteristics of Reverse-Cope Cyclizations of Homoallylic Sulfoxide Nitrone Adducts: A Highly Stereoselective Route to Pyrrolidine-N-oxides

Jane R. Hanrahan* , David W. Knight, Rhys Salter
  • *Chemistry Department, Cardiff University, P.O. Box 912, Cardiff CF10 3TB, UK; Fax + 44(29)20 87 42 10; E-mail: knightdw@cf.ac.uk
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Publication Date:
27 September 2001 (online)

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Lithiated homoallylic sulfoxides 4 add smoothly to a selection of aldonitrones to give largely single diastereoisomers of the unsaturated hydroxylamines 5 which undergo reverse Cope cyclizations to give the highly substituted pyrrolidine-N-oxides 6 in a stereocontrolled manner.

homoallylic sulfoxides - aldonitrones - unsaturated hydroxylamines - reverse Cope cyclizations - pyrrolidine-N-oxides