«it's a (Kinetic) Trap!» - Selectively Differentiating Allylic Azide Isomers

Joseph J. Topczewski, Matthew R. Porter

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


Allylic azides are known to undergo the Winstein rearrangement and are often isolated as an equilibrating mixture of isomers. While this process has been known for almost 60 years, very few synthetic applications of this process have been reported. The absence of methods exploiting these intermediates likely stems from a paucity of approaches for gaining the required selectivity to differentiate the isomers. Our lab has made some progress in leveraging this unusual reaction into practical synthetic methodology. Presented herein is a summary of our lab's recent accomplishments in selectively trapping allylic azides. 1 Introduction 2 Background: Allylic Azides 3 Dynamic Cyclization of Imidates 4 Summary and Outlook.

Original languageEnglish (US)
Pages (from-to)1537-1542
Number of pages6
Issue number12
StatePublished - Jul 24 2018

Bibliographical note

Funding Information:
Financial support was provided by the University of Minnesota and The American Chemical Society’s Petroleum Research Fund (PRF # 56505-DNI1). This research was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award Number R35GM124718.The Amecrain Chemcail Soecsiy’ Peotelum Research Fund 5(6505-DN1IN)oaitnal nIutsitet of Genearl Medcail Secinces R(35GM124718)

Publisher Copyright:
© Georg Thieme Verlag Stuttgart.

Copyright 2018 Elsevier B.V., All rights reserved.


  • allylic
  • azides
  • cyclization
  • dynamic kinetic resolution
  • stereoselective
  • synthesis


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