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Generation and reactions of novel oxiranyl ‘Remote’ anions |
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| Authors: | A ChaiyanurakkulR Jitchati M KaewpetS Rajviroongit Y Thebtaranonth P ThongyooW Watcharin |
| Institution: | a Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand b National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Patumthani 12120, Thailand c Department of Chemistry, Faculty of Science, Thammasart University, Patumthani 12120, Thailand |
| Abstract: | Deprotonation 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. |
| Keywords: | oxiranyl anion remote anion oxirane β-lithiation stereoselective deprotonation |
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