Synlett 2018; 29(12): 1537-1542
DOI: 10.1055/s-0037-1609479
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© Georg Thieme Verlag Stuttgart · New York

"It’s a (Kinetic) Trap!" – Selectively Differentiating Allylic Azide Isomers

Department of Chemistry, University of Minnesota - Twin Cities, 207 Pleasant St. SE, Minneapolis MN 55455, USA   Email: jtopczew@umn.edu
,
Matthew R. Porter
Department of Chemistry, University of Minnesota - Twin Cities, 207 Pleasant St. SE, Minneapolis MN 55455, USA   Email: jtopczew@umn.edu
› Author Affiliations
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.
Further Information

Publication History

Received: 14 February 2018

Accepted after revision: 16 March 2018

Publication Date:
12 April 2018 (online)

Abstract

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

 
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