Gündoğdu, ÖzlemAtalay, AbdurrahmanÇelebioğlu, NeslihanAnıl, BarışŞahin, ErtanŞanlı Mohamed, GülşahBozkaya, UğurKara, Yunus2022-06-232022-06-2320222228602228600022-2860https://doi.org/10.1016/j.molstruc.2022.133163https://hdl.handle.net/11147/12087The 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.eninfo:eu-repo/semantics/embargoedAccessEpoxy alcoholTheorical computationsRegioselectivityArticle2-s2.0-8513016881810.1016/j.molstruc.2022.133163