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Synthesis 2017; 49(15): 3183-3214
DOI: 10.1055/s-0036-1588452
DOI: 10.1055/s-0036-1588452
review
Keteniminium Ions: Unique and Versatile Reactive Intermediates for Chemical Synthesis
Our work was supported by the Université libre de Bruxelles (ULB) and the FNRS (CDR J.0058.17 Keteniminium). M.L. and C.T. acknowledge the Fonds pour la formation à la Recherche dans l’Industrie et dans l’Agriculture (F.R.I.A.) for graduate fellowshipsFurther Information
Publication History
Received: 15 May 2017
Accepted after revision: 16 May 2017
Publication Date:
17 July 2017 (online)
Dedicated to Prof. Herbert Mayr, a truly inspiring chemist, on the occasion of his 70th birthday
Abstract
Keteniminium ions have been demonstrated to be remarkably useful and versatile reactive intermediates in chemical synthesis. These unique heterocumulenes are pivotal electrophilic species involved in a number of efficient and selective transformations. More recently, even more reactive ‘activated’ keteniminium ions bearing an additional electron-withdrawing group on the nitrogen atom have been extensively investigated. The chemistry of these unique reactive intermediates, including representative methods for their in situ generation, will be overviewed in this review article.
1 Introduction
2 The Chemistry of Keteniminium Ions
3 The Chemistry of Activated Keteniminium Ions
4 Keteniminium Ions: Pivotal Intermediates for the Synthesis of Natural and/or Biologically Relevant Molecules
5 Conclusions and Perspectives
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For examples of characterization of keteniminium ions, see:
For reviews on the activation of amides with triflic anhydride, see:
For major references on the use of 2-halopyridines in the electrophilic activation of amides, see:
For other representative examples yielding 3-amino-2H-azirines, see:
For additional examples of reaction that could proceed through intramolecular trapping of an intermediate keteniminium ion with a nucleophile, see:
Also see:
For other examples of intermolecular [2+2] cycloadditions with keteniminium ions, see:
For reviews, see:
For representative selected examples, see:
For a similar reaction with gold catalysis, see:
For examples, see:
For a review on gold-catalyzed cyclization of ynamides, see:
Also see:
Also see: