Synthesis of new trisubstituted hexahydro-isoindole-1,3-dione derivatives regio- and stereoselectivity: spectroscopic and theoretical studies

Abstract

2-Hydroxy-5-alkylhexahydro-4H-oxireno[2,3-e]isoindole-4,6(5H)-diones were synthesized, and their C-2 selective ring opening products were obtained through nucleophilic additions such as with MeOH. The methoxydiols obtained from the ring-opening reactions were converted to corresponding acetate derivatives. The structures of the methoxydiacetates were determined by H-1 and C-13 NMR and X-ray analyses. Furthermore, theoretical computations were carried out to explain the regioselectivity in the ring-opening reaction of epoxy alcohols. The theoretical calculations showed that the ring-opening reaction of epoxy alcohols proceeds in a thermodynamically controlled manner and regioselectivity occurs depending on the stability of the intermediate.[GRAPHICS]