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

GÜNDOĞDU Ö., Atalay A., Celebioglu N., ANIL B., ŞAHİN E., Sanli-Mohamed G., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1264, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1264
  • Publication Date: 2022
  • Doi Number: 10.1016/j.molstruc.2022.133163
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Keywords: Epoxy alcohol, Ring opening, Regioselectivity, Theorical computations, Isoindole-1,3-dione, SUBSTITUTION-REACTIONS, REARRANGEMENT, 1,2-EPOXIDES, MECHANISMS, ACIDS
  • Hacettepe University Affiliated: Yes

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 N-3(-). 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. (c) 2022 Published by Elsevier B.V.