Naslov
Synthesis of propargylic epoxides

Autori
Kolman, Robert Junior ; Dokli, Irena

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Simpozij studenata doktorskih studija PMF-a : knjiga sažetaka = PhD student symposium 2021 : book of abstracts / Barišić, Dajana - Zagreb : Prirodoslovno-matematički fakultet Sveučilišta u Zagrebu, 2021, 338-338

ISBN
978-953-6076-90-1

Skup
5. Simpozij studenata doktorskih studija PMF-a = 5th Faculty of Science PhD Student Symposium

Mjesto i datum
Zagreb, Hrvatska, 24.04.2021. - 25.04.2021

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
propargylic epoxide ; Sonogashira ; epoxidation ; halohydrin dehalogenase

Sažetak
The synthesis of substituted propargylic epoxides for the purpose of stereoselective and regioselective ring opening by enzyme halohydrin dehalogenase was described. Using different nucleophiles, enantiomerically pure propargylic azidoalchohols and bicyclic triazole derivatives (N3-), propargylic oxazolidinone derivatives (OCN-) and propargylic nitriloalchohols (NC-) could be obtained [1]. Phenyl-, tert-butyl- and cyclopentyl- substituted epoxides were synthesized from the corresponding terminal acetylenes by introduction and epoxidation of a double bond. Also, p- and mtolyl derivatives were synthesized in a similar reaction sequence, starting from the corresponding iodotoluene and trimethylsilylacetylene. Furthermore, attempts to prepare the phenyl derivative in two ways (in a reaction sequence similar to the synthesis of tolyl derivatives ; and by derivatization of propargyl alchohol, oxidation of the obtained alchohol to aldehyde in several ways and its cyclization by sulfonium ylides), as well as the p-tolyl derivative by reacting p- iodotoluene with ethynylmagnesium bromide, were described.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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