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Molecules 2015, 20(10), 18482-18495; doi:10.3390/molecules201018482

A Mild and Regioselective Ring-Opening of Aziridines with Acid Anhydride Using TBD or PS-TBD as a Catalyst

Department of Science Education, Faculty of Education, Ibaraki University, Ibaraki 310-8512, Japan
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Author to whom correspondence should be addressed.
Academic Editor: Choon-Hong Tan
Received: 2 September 2015 / Revised: 22 September 2015 / Accepted: 23 September 2015 / Published: 9 October 2015
(This article belongs to the Special Issue Brønsted Base Catalysis in Organic Synthesis)
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Abstract

The ring-opening of N-tosylaziridines with various acid anhydrides catalyzed by 5 mol % of 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) afforded the corresponding β-amino esters in excellent yields under mild reaction conditions. Polymer-supported catalyst, PS-TBD also acts as a good catalyst for this reaction. PS-TBD was easily recovered and reused with minimal loss of activity. View Full-Text
Keywords: organocatalyst; basecatalyst; polymercatalyst; guanidine; aziridine; amino alcohols organocatalyst; basecatalyst; polymercatalyst; guanidine; aziridine; amino alcohols
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Matsukawa, S.; Mouri, Y. A Mild and Regioselective Ring-Opening of Aziridines with Acid Anhydride Using TBD or PS-TBD as a Catalyst. Molecules 2015, 20, 18482-18495.

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