Title of article
Ethynyloxirane anions: a new tool for natural product synthesis
Author/Authors
Sophie Klein، نويسنده , , Jing H Zhang، نويسنده , , Michel Holler، نويسنده , , Jean-Marc Weibel، نويسنده , , Patrick Pale، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2003
Pages
10
From page
9793
To page
9802
Abstract
Ethynyl oxiranes can be deprotonated with nBuLi in THF and trapped with various electrophiles, providing a stereoselective access to trisubstituted oxiranes. Alkyl iodides and aldehydes react readily with the ethynyloxiranyl anions but not sulfonyl derivatives. Mechanistic investigations highlighted the stabilizing role of the ethynyl group, the localization of the anion and the coordinating role of the oxirane oxygen atom during deprotonation.
Keywords
Deprotonation , Oxirane , ethynyl oxiranes
Journal title
Tetrahedron
Serial Year
2003
Journal title
Tetrahedron
Record number
1084527
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