Download PDF
Synlett 2000; 2000(8): 1193-1195
DOI: 10.1055/s-2000-6762
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 Transannular Radical Cyclization of Unsaturated Cyclic Iodoacetals Yielding Medium-sized Carbocycles

Hajime Nagano* , Asako Tada, Yuko Isobe, Tomoko Yajima
  • *Department of Chemistry, Faculty of Science, Ochanomizu University, Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan; Fax + 81-3-59 78-58 98; E-mail: nagano@cc.ocha.ac.jp
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Iodoacetalization of (Z)-allylic alcohols 1a - 1c in high dilution followed by transannular radical cyclization gave cis-fused bicyclic acetals 5a - 5c and 6a - 6c with high diastereoselectivities (84-93% de) and in 54-62% yields. The reaction of 2a gave 5a and 6a with 77% de, but in low yield. However, the sequential reaction of the higher homologue 1d and (E)-allylic alcohols 2b - 2d showed poor diastereoselectivities.

radical reactions - transannular cyclizations - iodo acetals - medium-sized rings - diastereoselectivity

      >