X=Y-ZH system as potential 1,3-dipoles. Part 59: Cascade 1,3-azaprotio cyclotransfer-1,3-dipolar cycloaddition (1,3-APT-1,3-DC) reactions of benzobicyclo[3.3.1]non-5-en-9-one oxime


DÖNDAŞ H. A., Fishwick C., Grigg R., Thornton-Pett M.

TETRAHEDRON, vol.59, no.50, pp.9997-10007, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 59 Issue: 50
  • Publication Date: 2003
  • Doi Number: 10.1016/j.tet.2003.10.027
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.9997-10007
  • Çukurova University Affiliated: No

Abstract

Preparation of some novel spiro-oxazolidines related to 3, which is known to posses anorectic and antidepressant activity, via 1,3-APT- 1,3-DC cascades of the oxime of benzobicyclo[3.3. 1]non-5-en-9-one 1 is described. Substrate I allows the influence of the two bridges on the cascade to be assessed with respect to the configuration of the nitrone that is generated and the facial selectivity of the subsequent cycloaddition. (C) 2003 Elsevier Ltd. All rights reserved.