The Evans–Tishchenko Reaction: Scope and Applications

Kevin J. Ralston; Alison N. Hulme

doi:10.1055/s-0032-1316544

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(15): 2310-2324
DOI: 10.1055/s-0032-1316544

short review

The Evans–Tishchenko Reaction: Scope and Applications

Kevin J. Ralston

EaStCHEM, School of Chemistry, Joseph Black Building, Kings Buildings, West Mains Road, Edinburgh, EH9 3JJ, UK, Fax: +44(131)6504743 eMail: Alison.Hulme@ed.ac.uk

,

Alison N. Hulme*

EaStCHEM, School of Chemistry, Joseph Black Building, Kings Buildings, West Mains Road, Edinburgh, EH9 3JJ, UK, Fax: +44(131)6504743 eMail: Alison.Hulme@ed.ac.uk

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Abstract

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Abstract

The Evans–Tishchenko reaction provides a highly diastereoselective route towards the synthesis of 1,3-anti diol monoesters, and therefore has found prominent use in a number of synthetic applications. This review summarises recent applications of the Evans–Tishchenko reaction in natural product synthesis, and examines scope in terms of substrate range, functional group tolerance, and catalyst.

1 Introduction

2 Reaction Mechanism and Catalyst Scope

2.1 Reaction Mechanism

2.2 Samarium

2.3 Scandium

2.4 Zirconium

2.5 Other Metals

3 Substrate Scope

4 Application in Natural Product Synthesis

4.1 Protection/Asymmetric Induction

4.2 Functional Group Interconversion

4.3 Fragment Linkage and Ring Formation

5 Future Perspectives

6 Conclusion

Key words

Evans–Tishchenko reaction - anti-1,3-diols - diastereoselectivity - Lewis acids - samarium - natural products

Volltext

Referenzen

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