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.
Original language | English |
---|---|
Pages (from-to) | 2473-2483 |
Number of pages | 11 |
Journal | Synthesis |
Issue number | 17 |
DOIs | |
State | Published - 2002 |
Externally published | Yes |
Keywords
- Stereoselectivity
- Vinyl enol ethers
- Vinyl sulfides
- Vinyl sulfones
- Vinyl sulfoxides
- Zirconocene complexes
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry