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.
Highlights
Aziridines are very useful intermediates for the synthesis of numerous nitrogen-containing biologically active compounds [1,2,3]
The ring-opening of aziridines with water is the most common method to prepare free β-amino alcohols
The ring-opening reaction of aziridines with acid or acid anhydrides as the nucleophiles have been recently studied
Summary
Aziridines are very useful intermediates for the synthesis of numerous nitrogen-containing biologically active compounds [1,2,3]. Β-amino alcohols, which can be synthesized from the nucleophilic ring-opening reactions of aziridines are useful intermediates in organic synthesis [4,7]. The ring-opening reaction of aziridines with acid or acid anhydrides as the nucleophiles have been recently studied. To develop of a more efficient reaction, we examined the use of TBD (1,5,7-Triazabicyclo[4,4,0]dec-5-ene) as a catalyst. Many unique reactions have been reported using TBD as an organocatalyst, such as the Henry reaction [31], Wittig and Horner-Wadsworth-Emmons reaction [32], Michael reaction [33], ring-opening polymerization [34], conjugate addition to activated alkenes [35], aminolysis of esters [36,37], intramolecular aldol reaction [38], and synthesis of pyrazolines [39], etc. We report that TBD acts as an effective organobase catalyst for the ring-opening reaction of aziridines with acid anhydride
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