Synthesis 2018; 50(09): 1750-1772
DOI: 10.1055/s-0036-1589529
review
© Georg Thieme Verlag Stuttgart · New York

Claisen Rearrangements of Benzyl Vinyl Ethers and Heterobenzyl Vinyl Ethers

Jed M. Burns
The University of Queensland, School of Chemistry and Molecular Biosciences, St Lucia Campus, Brisbane, Qld 4072, Australia   eMail: r.mcgeary@uq.edu.au
,
Elizabeth H. Krenske
The University of Queensland, School of Chemistry and Molecular Biosciences, St Lucia Campus, Brisbane, Qld 4072, Australia   eMail: r.mcgeary@uq.edu.au
,
Ross P. McGeary*
The University of Queensland, School of Chemistry and Molecular Biosciences, St Lucia Campus, Brisbane, Qld 4072, Australia   eMail: r.mcgeary@uq.edu.au
› Institutsangaben
We thank the Australian Research Council (FT120100632 to E. H. K.) for financial support.
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Publikationsverlauf

Received: 13. November 2017

Accepted after revision: 15. November 2017

Publikationsdatum:
07. März 2018 (online)


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