Synlett 2014; 25(17): 2379-2384
DOI: 10.1055/s-0034-1378531
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© Georg Thieme Verlag Stuttgart · New York

Stereoselectivity of Metal-Catalyzed Cyclizations of 1,6-Dienes

Christophe Aïssa*
University of Liverpool, Department of Chemistry, Crown Street, L69 7ZD, Liverpool, UK   Fax: +44(151)7943588   Email: aissa@liverpool.ac.uk
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Further Information

Publication History

Received: 29 May 2014

Accepted after revision: 24 June 2014

Publication Date:
25 August 2014 (online)

Abstract

In this article, the stereoselectivity of metal-catalyzed cyclizations of 1,6-dienes is examined according to the elementary steps which can be envisaged as triggers of the rearrangements. Crucial results have been obtained which demonstrate that enantio­selective and diastereoselective cyclizations are possible. However, a lack of stereoselectivity is often observed for 1,6-dienes having a prochiral tether, which appears to originate in the lack of differentiation between the two olefins of the substrates.

1 Introduction

2 Oxidative Cyclometalation

3 Copper-Catalyzed Photocycloaddition

4 Intermolecular Hydrometalation

5 Carbometalation and Sila-Metalation

6 π-Allyl Formation in Metallo-Ene Cyclization

7 Olefin Electrophilic Activation

8 C–H Activation

9 Conclusion

 
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