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

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

Key words

cyclization - metal catalysis - 1,6-dienes - stereoselectivity - C–H activation

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