X=Y-ZH systems as potential 1,3-dipoles. Part 21 activation of the ZH proton in imines.

Ronald Grigg*, Gregory Donegan, H. Q.Nimal Gunaratne, Deirdre A. Kennedy, John F. Malone, Visuvanathar Sridharan, Sunit Thianpatanagul

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

72 Citations (Scopus)


Imines, RCH=N-ZH, possessing a range of ZH groups (Z=CHCOPh, CHCOSR, CHCONHR, CHP(O)(OEt)2, 2-CH-pyridyl, 2-CH-thiazolyl, and 9-fluorenyl) undergo thermal 1,2-prototropy generating azomethine ylides stereospecifically. The intermediate azomethine ylides undergo cycloaddition reactions with dipolarophiles either via an endo-transition state or via both endo- and exo-transition states to give polyfunctional pyrrolidines in good yield. In certain instances involving imines in which the amide activating group is present, the imine catalyses cis ⇌ trans isomerisation of the dipolarophile. X-Ray crystal structures of two of the cycloadducts are reported.

Original languageEnglish
Pages (from-to)1723-1746
Number of pages24
Issue number6
Publication statusPublished - 1989

Bibliographical note

Copyright 2014 Elsevier B.V., All rights reserved.

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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