Download PDF
Synlett 1993; 1993(2): 158-162
DOI: 10.1055/s-1993-22388
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 Formation of trans-Decalin and cis-Decalin Skeletons via Hydroxy Group Directed Cyclization Induced by Samarium(II) Iodide

Makoto Kito* , Toshinari Sakai, Kaori Yamada, Fuyuhiko Matsuda, Haruhisa Shirahama
  • *Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060, Japan
Further Information

Publication History

Publication Date:
19 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

By treating the anti-hydroxyketones (1 and 2) and the syn-hydroxyketones (4 and 5) with samarium(II) iodide, the ketone-olefin coupling cyclizations took place in a stereocontrolled manner to give the trans-decalin diol (3) and the epimeric mixtures of the cis-decalin diols (6 and 7) respectively. The observed stereochemistries on the reductive coupling products are established by chelation of the samarium(III) cation generated in the process, with the hydroxyl groups incorporated in the starting materials.

      >