Spiro- and bridged-ring forming electrophile induced ->oxime->nitrone cycloaddition cascades. Multiplication of chirality

DÖNDAŞ H. A., Grigg R., Frampton C.

TETRAHEDRON LETTERS, vol.38, no.32, pp.5719-5722, 1997 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 38 Issue: 32
  • Publication Date: 1997
  • Doi Number: 10.1016/s0040-4039(97)01255-0
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5719-5722
  • Çukurova University Affiliated: No

Abstract

Electrophile induced 6-exo-trig spirocyclisation of oximes onto 5-, 6- or 7-membered cycloalkenes occurs stereo- and regio- specifically in good yield. Bridged - ring forming cyclisations creating bicycle-[3.3.1]- and bicyclo-[3.2.1]-ring systems also occur in good yield. Chiral bridged-ring systems have been synthesised, via the latter processes, that involve multiplication of chiral centres from one to six and seven in one pot reactions. (C) 1997 Elsevier Science Ltd.