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Coupling reactions of enyne oxiranes with Grignard reagents

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MasterThesis (12.13Mb)
Date
2016-10
Author
Aytaç, İsmet Arınç
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Abstract
Laboratory-synthesized (Z)-2,4-Enyne oxiranes were subjected iron-catalyzed reactions with Grignard reagents. The reactions afforded majorly E-configured vinylallenes with a hydroxyl group on the allylic carbon as the 1,5-(SN2'')-substitution products. However, in some case, along with the desired vinyllallenes products, 1,1- (SN2) and 1,3-substitution (SN2’) by-products were also recovered. Diastereo-selectivity of the method is strictly reliant on the syn/anti mode of the alkylation process. This study provides a new methodology for the synthesis of vinylallenes which are potential building blocks of biological active molecules.
 
Laboratuvarda sentezlenen (Z)-2,4-enin oksiran bileşiklerinin Grignard reaktifleri ile demir katalizli tepkimeleri gerçekleştirilmiştir. Bu tepkimeler ana ürün olarak 1,5-(SN2”)-sübstitüsyon ürünü olan E-konfigürasyona sahip allilik pozisyonunda hidroksil grubu bulunan vinilallen ürünleri vermektedir. 1,1-(SN2) ve 1,3-(SN2) ürünleri de bazı reaktiflerin tepkimelerinde oluşabilmektedir. Tepkimenin diastereo seçimliliği alkilasyonun yalnızca syn ya da anti modunda gerçekleşmesine bağlıdır. Bu çalışma, biyolojik olarak aktif moleküllerin çeşitli yapı taşları olabilecek vinylallen sentezi için yeni bir yöntem sunmaktadır.
 
URI
http://hdl.handle.net/11147/5700
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  • Master Degree / Yüksek Lisans Tezleri [1679]


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