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A mechanistically unusual base induced [1,3]-H-shift in homoallylic ethers

✍ Scribed by Johann Mulzer; Gregor Wille; Jörn Bilow; Duilio Arigoni; Bruno Martinoni; Konrad Roten

Book ID: 104257578
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 198 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)01223-9

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✦ Synopsis

Upon treatment with Nail in DMF the homoallylic ethers lag and the amine lh undergo a rearrangement into the trisubstituted (E)-olefins 2a-h. Experiments with isotopically labelled forms of la and lb show that the [1,3]-shift is cleanly intramolecular and proceeds predominantly in the suprafacial mode.

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