New Preparation of sp2 Organometallic Derivatives

Nicka Chinkov; Helena Chechik; Swapan Majumdar; Ilan Marek; Annie Liard

doi:10.1055/s-2002-35622

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New Preparation of sp² Organometallic Derivatives

Nicka Chinkov, Helena Chechik, Swapan Majumdar, Ilan Marek*, Annie Liard
Department of Chemistry and Institute of Catalysis Science and Technology, Technion-Israel Institute of Technology, Haifa 32000, Israel.
Fax: +972(4)8293709; e-Mail: chilanm@tx.technion.ac.il;

Abstract

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Abstract

Various polysubstituted, metalated olefins are easily prepared from heterosubstituted alkenes such as vinyl enol ethers, vinyl sulfides, sulfoxides and even sulfones in a one-step procedure. A complete isomerization was observed in this process, which leads only to the E isomer.

1 Introduction
1.1 Oxidative Metallation of Organic Halides
1.2 Metal-Halogen Exchange
1.3 Metal-Hydrogen Exchange
1.4 Hydrometallation Reactions
1.5 Carbometallation Reactions
1.6 Transmetallation Reactions
1.7 The Shapiro Reaction
2 Limitations of these Methods
3 Zirconocene Complexes in Organic Synthesis
4 Discussion
4.1 Vinylic Enol Ether into Vinylic Organometallic Derivatives
4.1.1 Mechanistic Discussion
4.2 Vinylic Thioenol Ether into Vinylic Organometallic Derivatives
4.3 Vinyl Sulfoxides into Vinylic Organometallic Derivatives
4.4 Vinyl Sulfones into Vinylic Organometallic Derivatives
5 Conclusions

Key words

sp² organometallics - vinyl sulfides - vinyl sulfones - vinyl enol ethers - vinyl sulfoxides - zirconocene complexes - stereoselectivity

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