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

Satoru Matsukawa; Yasutaka Mouri

doi:10.3390/molecules201018482

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

Molecules. 2015 Oct 9;20(10):18482-95. doi: 10.3390/molecules201018482.

Authors

Satoru Matsukawa¹, Yasutaka Mouri²

Affiliations

¹ Department of Science Education, Faculty of Education, Ibaraki University, Ibaraki 310-8512, Japan. satoru.matsukawa.1@vc.ibaraki.ac.jp.
² Department of Science Education, Faculty of Education, Ibaraki University, Ibaraki 310-8512, Japan. c32amg777@yahoo.co.jp.

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.

Keywords: amino alcohols; aziridine; basecatalyst; guanidine; organocatalyst; polymercatalyst.

MeSH terms

Amino Alcohols / chemistry
Anhydrides / chemistry*
Azabicyclo Compounds / chemistry*
Aziridines / chemistry*
Catalysis
Esters
Molecular Structure
Stereoisomerism

Substances

Amino Alcohols
Anhydrides
Azabicyclo Compounds
Aziridines
Esters
triazabicyclodecene