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Synthesis 2009(22): 3769-3774
DOI: 10.1055/s-0029-1218151
DOI: 10.1055/s-0029-1218151
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of N-Activated Aziridines of Long-Chain Fatty Acid Esters
Weitere Informationen
Received
27 April 2009
Publikationsdatum:
07. Oktober 2009 (online)
Publikationsverlauf
Publikationsdatum:
07. Oktober 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200922/lookinside/thumbnails/10.1055-s-0029-1218151-1.jpg)
Abstract
An alternative one-step synthesis of N-activated aziridines of naturally occurring fatty acid esters from olive oil and sunflower oil has been achieved. N-Tosylaziridine derivatives were obtained in yields ranging from 8.5 to 97.5%. Methyl cis- and trans-8-(3-octyl-1-tosylaziridin-2-yl)octanoates were formed with transesterified olive oil as substrate, and methyl cis- and trans-(Z)-11-(3-pentyl-1-tosylaziridin-2-yl)undec-9-enoates were produced when transesterified sunflower oil was the substrate.
Key words
aziridination - copper(II) acetylacetonate - olive oil methyl esters - sunflower oil methyl esters
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