Ethynyloxirane anions: a new tool for natural product synthesis |
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| Authors: | Sophie KleinJing H Zhang Michel HollerJean-Marc Weibel Patrick Pale |
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| Affiliation: | Laboratoire de synthèse et réactivité organique, associé au CNRS, Institut Le Bel, Université Louis Pasteur, 4 rue B. Pascal, 67000 Strasbourg, France |
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| 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. |
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| Keywords: | ethynyl oxiranes deprotonation oxirane |
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