Publication: Pyridine stabilized oxiranyl remote anions
Issued Date
2009-07-22
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ISSN
00404039
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2-s2.0-66549098790
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Mahidol University
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SCOPUS
Bibliographic Citation
Tetrahedron Letters. Vol.50, No.29 (2009), 4217-4220
Suggested Citation
Pattama Saisaha, Chakkrapan Nerungsi, Supitchaya Iamsaard, Tienthong Thongpanchang Pyridine stabilized oxiranyl remote anions. Tetrahedron Letters. Vol.50, No.29 (2009), 4217-4220. doi:10.1016/j.tetlet.2009.04.106 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/27176
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Title
Pyridine stabilized oxiranyl remote anions
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Abstract
The chemistry of oxiranyl remote anions derived from α,β-epoxypyridines is investigated. Deprotonation of α,β-epoxy pyridines at the β-position and reactions of the corresponding anions with a variety of electrophiles are found to be highly regioselective, possibly as a consequence of stabilization from the chelation between lithium and the pyridine moiety in the form of a five-membered cyclic intermediate. © 2009 Elsevier Ltd. All rights reserved.