X=Y-ZH Systems as potential 1,3-dipoles. Part 54: Stereo- and facially-selective formation of bridged bicyclic N-heterocycles via a sequential one-pot electrophile induced oxime -> nitrone -> cycloaddition sequence. Multiplication of chirality

DÖNDAŞ H. A., Grigg R., Thibault S., Thomas W., Thornton-Pett M.

TETRAHEDRON, vol.58, no.29, pp.5827-5836, 2002 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 58 Issue: 29
  • Publication Date: 2002
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5827-5836
  • Çukurova University Affiliated: No

Abstract

Electrophile induced bridged-ring forming cyclisations creating azabicyclo-[3.3.1]- and azabicyclo-[3.2.1]-nitrones, followed by cycloaddition, occur stereo-, regio- and facially specifically in good to excellent yield. Chiral bridged-ring systems have been synthesised that involve multiplication of chiral centres from one to six and one to seven in one pot reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.