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Title: Regio- and stereo-chemical ring-opening reactions of the 2,3-epoxy alcohol derivative with nucleophiles: Explanation of the structures and C-2 selectivity supported by theoretical computations
Authors: Gündoğdu, Özlem
Atalay, Abdurrahman
Çelebioğlu, Neslihan
Anıl, Barış
Şahin, Ertan
Şanlı Mohamed, Gülşah
Bozkaya, Uğur
Kara, Yunus
Ahi Evran Üniversitesi
Hacettepe Üniversitesi
Atatürk Üniversitesi
Atatürk Üniversitesi
Atatürk Üniversitesi
Izmir Institute of Technology
Hacettepe Üniversitesi
Atatürk Üniversitesi
Keywords: Epoxy alcohol
Theorical computations
Issue Date: Sep-2022
Publisher: Elsevier
Abstract: The ring-opening reactions of (1aS,2S,6bR)-5-ethyl-2-hydroxyhexahydro-4H-oxireno[2,3-e]isoindole-4,6(5H)-dione were investigated under very mild and nonchelated conditions. C-2 selective ring-opening products were obtained with nucleophilic additions such as Cl−, Br− and N3−. The exact configuration of (3aS,4R,5R,6S,7aS)-5-chloro-2-ethyl-4,6-dihydroxyhexahydro-1H-isoindole-1,3(2H)-dione was determined by X-Ray diffraction analysis which was obtained from the reaction of epoxy alcohol with HCl. On the other hand, theoretical computations were carried out to explain the regioselectivity in the ring opening reaction of epoxy alcohols. The results showed that the ring-opening reaction of both epoxy alcohols proceeds in a kinetically controlled manner and regioselectivity occurs depending on the transition state.
Appears in Collections:Chemistry / Kimya
Scopus İndeksli Yayınlar Koleksiyonu / Scopus Indexed Publications Collection
WoS İndeksli Yayınlar Koleksiyonu / WoS Indexed Publications Collection

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