Tetrahedron Letters p. 5469 - 5472 (1997)
Update date:2022-08-03
Topics:
Mulzer, Johann
Wille, Gregor
Bilow, Joern
Arigoni, Duilio
Martinoni, Bruno
Roten, Konrad
Upon treatment with NaH in DMF the homoallylic ethers 1a-g and the amine 1h undergo a rearrangement into the trisubstituted (E)-olefins 2a-h. Experiments with isotopically labelled forms of 1a and 1b show that the [1,3]-shift is cleanly intramolecular and proceeds predominantly in the suprafacial mode.
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