Acyclic bis-allylic ethers undergo,syn or anti stereoselective[2,3]-Wittig rearrangementto give homoallylic alcohols dependingon the substituents,and E-selective tandem [2,3]-Wittig-anionic oxy-Coperearrangementto give 8,&-unsaturated aldehydes. O 1997Elsevier ScienceLtd.
✦ LIBER ✦
On the Reactivity of o -Lithioaryl Ethers: Tandem Anion Translocation and Wittig Rearrangement
✍ Scribed by Barluenga, José; Fañanás, Francisco J.; Sanz, Roberto; Marcos, César; Trabada, Marta
- Book ID
- 118735849
- Publisher
- American Chemical Society
- Year
- 2002
- Tongue
- English
- Weight
- 54 KB
- Volume
- 4
- Category
- Article
- ISSN
- 1523-7060
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The tztled szgmatropzc sequence proceeds wzth compZete net retentzon of confzguratzon, and surprzszngly, suffers from a regzochemzcal compZccat-z,on arzstng maznly from the unexpected competztzon of the i2,37-vs. L-1,23-shzft zn the Wzttzg process, as reveaZed by the use of the deuterzwn-labeled sub