Synthesis 2013; 45(9): 1121-1159
DOI: 10.1055/s-0032-1316869
review
© Georg Thieme Verlag Stuttgart · New York

Claisen Rearrangement of Aliphatic Allyl Vinyl Ethers from 1912 to 2012: 100 Years of Electrophilic Catalysis

Julia Rehbein
a   Fachbereich Chemie, Institut für Organische Chemie, Universität Hamburg, 20146 Hamburg, Germany
,
Martin Hiersemann*
b   Fakultät Chemie, Technische Universität Dortmund, 44227 Dortmund, Germany   Email: martin.hiersemann@udo.edu
› Author Affiliations
Further Information

Publication History

Received: 06 January 2013

Accepted after revision: 12 February 2013

Publication Date:
17 April 2013 (online)


Abstract

This review summarizes, from a personal perspective, the development of catalytic asymmetric Claisen rearrangements from 1912 to 2012.

1 Introduction

2 Gosteli–Claisen Rearrangement

3 Claisen Rearrangement Using Stable Enols: Kojic Acid and Diosphenols

4 The Early Years: Catalysis by Brønsted Acids

5 Lewis Acid Mediated Claisen Rearrangements: The Aluminum Age

6 Catalysis by Precious Metals

7 Catalysis by σ-Lewis Acids

8 Catalysis by Achiral Organocatalysts

9 Catalytic Asymmetric Claisen Rearrangements

10 Conclusion