Stereoselective electrophile-induced mono- and bis-cyclisation-fragmentation reactions of alkenyl oxime O-allyl and O-benzyl ethers. Synthesis of dihydropinidine

DÖNDAŞ H. A., Grigg R., Markandu J., Perrior T., Suzuki T., Thibault S., ...More

TETRAHEDRON, vol.58, no.1, pp.161-173, 2002 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 58 Issue: 1
  • Publication Date: 2002
  • Doi Number: 10.1016/s0040-4020(01)01118-8
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.161-173
  • Çukurova University Affiliated: No

Abstract

Phenylseleny bromide-induced cyclisation of gamma- and delta-unsaturated aldoxime and ketoxime O-allyl and O-benzyl ethers is followed by a slow fragmentation of the resultant oxyiminium ions furnishing cyclic iminium salts which are readily reduced to pyrrolidines, piperidines or tetrahydroisoquinolines by sodium borohydride; dialkenyl oximes yield indolizidines and quinolizidines by an analogous sequence terminating in a mercury(II)-induced cyclisation. (C) 2002 Elsevier Science Ltd. All rights reserved.