Publication: Generation and reactions of novel oxiranyl 'Remote' anions
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Issued Date
2003-12-01
Resource Type
ISSN
00404020
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2-s2.0-0242558387
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Mahidol University
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SCOPUS
Bibliographic Citation
Tetrahedron. Vol.59, No.49 (2003), 9825-9837
Suggested Citation
A. Chaiyanurakkul, R. Jitchati, M. Kaewpet, S. Rajviroongit, Y. Thebtaranonth, P. Thongyoo, W. Watcharin Generation and reactions of novel oxiranyl 'Remote' anions. Tetrahedron. Vol.59, No.49 (2003), 9825-9837. doi:10.1016/j.tet.2003.09.020 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/20677
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Title
Generation and reactions of novel oxiranyl 'Remote' anions
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. © 2003 Elsevier Ltd. All rights reserved.