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Synlett 2000; 2000(10): 1405-1407
DOI: 10.1055/s-2000-7637
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Stereoselective Synthesis of N-Hydroxypyrrolidines and Pyrrolidine-N-oxides by Cope-House Cyclization of Unsaturated Hydroxylamines Obtained from (2R,3S)-1,2-Epoxy-4-penten-3-ol

Andreas M. Palmer* , Volker Jäger
  • *Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany; Fax + 49-711-685 4321; E-mail: jager.ioc@po.uni-stuttgart.de
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Publication Date:
31 December 2000 (online)

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Ring opening of (2R,3S)-1,2-epoxy-4-penten-3-ol - obtained by asymmetric Sharpless epoxidation of divinylcarbinol - was effected with four hydroxylamines. The intermediate N-(4-pentenyl)-hydroxylamines underwent Cope-House cyclization to yield N-hydroxypyrrolidine-diols or pyrrolidine-N-oxide-diols.

Cope-House cyclization - epoxide - ring opening - unsaturated hydroxylamines - pyrrolidine-3,4-diols

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