Pyridine stabilized oxiranyl remote anions

Pattama Saisaha; Chakkrapan Nerungsi; Supitchaya Iamsaard; Tienthong Thongpanchang

doi:10.1016/j.tetlet.2009.04.106

Pyridine stabilized oxiranyl remote anions

Pattama Saisaha
, Chakkrapan Nerungsi
, Supitchaya Iamsaard
, Tienthong Thongpanchang

Department of Chemistry

Mahidol University
National Science and Technology Development Agency (NSTDA)

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4217-4220
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	29
DOIs	https://doi.org/10.1016/j.tetlet.2009.04.106
Publication status	Published - 22 Jul 2009

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10.1016/j.tetlet.2009.04.106

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title = "Pyridine stabilized oxiranyl remote anions",

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.",

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AU - Saisaha, Pattama

AU - Nerungsi, Chakkrapan

AU - Iamsaard, Supitchaya

AU - Thongpanchang, Tienthong

PY - 2009/7/22

Y1 - 2009/7/22

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/66549098790

U2 - 10.1016/j.tetlet.2009.04.106

DO - 10.1016/j.tetlet.2009.04.106

M3 - Article

AN - SCOPUS:66549098790

SN - 0040-4039

VL - 50

SP - 4217

EP - 4220

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

ER -

Pyridine stabilized oxiranyl remote anions

Abstract

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