Chemistry of Heterocyclic Compounds

, Volume 52, Issue 3, pp 146–148 | Cite as

Selected applications of N-protected (S)-2-(diazoacetyl)pyrrolidines (microreview)

  • Paulina Pipiak
  • Grzegorz Mlostoń

Open image in new window N-Protected (S)-2-(diazoacetyl)pyrrolidines can be considered as a group of the N-protected (S)-proline derivatives. They can be conveniently prepared from the corresponding acyl chloride or mixed anhydride via Arndt–Eistert reaction.1 In recent years, the N-protected (S)-2-(diazoacetyl)-pyrrolidines have been widely explored as easily available, chiral building blocks bearing the reactive diazo function and have found numerous applications for the multistep synthesis of more complicated heterocycles including some natural products and their analogs. Some of them are reported to display biological activities, e.g., antifungal,2 α4β2 nicotinic acetylcholine receptor-binding,3 , 4 oxygen free radical scavenging,5 and selective antihistamine.6 Three types of key reactions performed with N-protected (S)-2-(diazoacetyl)pyrrolidines are a) halogenation via treatment with HX agents and N2 elimination, b) catalytic decomposition and generation of reactive ketenes via the Wolff rearrangement of the intermediate α-oxo carbenes, and c) (3+2) cycloaddition reactions of the diazo 1,3-dipole with C=S dipolarophiles. In this article, mainly the papers from the period after 2001 are reviewed.


Carbene Halogenation Oxygen Free Radical Pyrrolidines Nicotinic Acetylcholine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Authors thank the National Science Center (Cracow, Poland) for generous financial support within the project Maestro (grant Maestro-3; Dec-2012/06/A/ST5/00219).


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© Springer Science+Business Media New York 2016

Authors and Affiliations

  1. 1.Department of Organic and Applied ChemistryUniversity of ŁódźŁódźPoland

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