Download PDF
Synlett 2000; 2000(10): 1405-1407
DOI: 10.1055/s-2000-7637
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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