A. ChaiyanurakkulR. JitchatiM. KaewpetS. RajviroongitY. ThebtaranonthP. ThongyooW. WatcharinMahidol UniversityThailand National Center for Genetic Engineering and BiotechnologyThammasat University2018-07-242018-07-242003-12-01Tetrahedron. Vol.59, No.49 (2003), 9825-9837004040202-s2.0-0242558387https://repository.li.mahidol.ac.th/handle/20.500.14594/20677Deprotonation of an oxiranyl β-proton takes place in a stereoselective manner providing the corresponding oxiranyl 'remote' anion. The anion is stabilized by chelation between the lithium and the carbonyl moiety of an ester, lactone, imide, or keto-group in the form of a five-membered cyclic intermediate. Certain ester-stabilized oxiranyl anions are stable and can be left in THF solution at -78°C for several hours. The generated anions undergo a stereoselective alkylation reaction to provide products, which could be useful intermediates in the synthesis of bioactive naturally occurring α-methylene bis-γ-butyrolactones. © 2003 Elsevier Ltd. All rights reserved.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryPharmacology, Toxicology and PharmaceuticsArticleSCOPUS10.1016/j.tet.2003.09.020