Claisen Rearrangements of Benzyl Vinyl Ethers and Heterobenzyl Vinyl Ethers

Abstract The Claisen rearrangement of benzylic substrates (benzyl vinyl­ ethers) has received considerably less attention than its well-known aliphatic and normal aromatic variants. Here, we review the rearrangement of both benzylic and heterobenzylic substrates, with examples of the reaction’s use...

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Veröffentlicht in:Synthesis (Stuttgart) 2018-05, Vol.50 (9), p.1750-1772
Hauptverfasser: Burns, Jed M., Krenske, Elizabeth H., McGeary, Ross P.
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract The Claisen rearrangement of benzylic substrates (benzyl vinyl­ ethers) has received considerably less attention than its well-known aliphatic and normal aromatic variants. Here, we review the rearrangement of both benzylic and heterobenzylic substrates, with examples of the reaction’s use in the synthesis of natural products and drug-like molecules. 1 Introduction 2 Early Attempts at the Benzyl-Claisen Rearrangement 3 Successful Benzylic Examples 4 Heterobenzylic Examples 5 Conclusion
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1589529