Generation and reactions of novel oxiranyl 'Remote' anions
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 cycl...
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th-mahidol.206772018-07-24T10:29:02Z Generation and reactions of novel oxiranyl 'Remote' anions A. Chaiyanurakkul R. Jitchati M. Kaewpet S. Rajviroongit Y. Thebtaranonth P. Thongyoo W. Watcharin Mahidol University Thailand National Center for Genetic Engineering and Biotechnology Thammasat University Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics 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. © 2003 Elsevier Ltd. All rights reserved. 2018-07-24T03:18:39Z 2018-07-24T03:18:39Z 2003-12-01 Article Tetrahedron. Vol.59, No.49 (2003), 9825-9837 10.1016/j.tet.2003.09.020 00404020 2-s2.0-0242558387 https://repository.li.mahidol.ac.th/handle/123456789/20677 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0242558387&origin=inward |
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Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics |
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Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics A. Chaiyanurakkul R. Jitchati M. Kaewpet S. Rajviroongit Y. Thebtaranonth P. Thongyoo W. Watcharin Generation and reactions of novel oxiranyl 'Remote' anions |
| description |
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. © 2003 Elsevier Ltd. All rights reserved. |
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Mahidol University |
| author_facet |
Mahidol University A. Chaiyanurakkul R. Jitchati M. Kaewpet S. Rajviroongit Y. Thebtaranonth P. Thongyoo W. Watcharin |
| format |
Article |
| author |
A. Chaiyanurakkul R. Jitchati M. Kaewpet S. Rajviroongit Y. Thebtaranonth P. Thongyoo W. Watcharin |
| author_sort |
A. Chaiyanurakkul |
| title |
Generation and reactions of novel oxiranyl 'Remote' anions |
| title_short |
Generation and reactions of novel oxiranyl 'Remote' anions |
| title_full |
Generation and reactions of novel oxiranyl 'Remote' anions |
| title_fullStr |
Generation and reactions of novel oxiranyl 'Remote' anions |
| title_full_unstemmed |
Generation and reactions of novel oxiranyl 'Remote' anions |
| title_sort |
generation and reactions of novel oxiranyl 'remote' anions |
| publishDate |
2018 |
| url |
https://repository.li.mahidol.ac.th/handle/123456789/20677 |
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1763498042308165632 |