Electroorganic Chemistry. XXVI. Electrooxidation of Enamines, Haloolefins, and Enol Ethers

Spiroketals via oxidative rearrangement of enol ethers.

Oxidative rearrangement of cyclic enol ethers leads to alpha-alkoxyesters. In the presence of a neighboring spiroether, this approach provides a stereoselective access to spiroketals. A modified proposal for the biosynthesis of acutumine is presented.

Zirconocene-catalyzed reactions of alkenyl-substituted enol ethers.

Oxidative Coupling of Enolates, Enol Silanes and Enamines: Methods and Natural Product Synthesis.

The oxidative coupling of enolates, enol silanes, and enamines provides a direct method for the construction of useful 1,4-dicarbonyl synthons. Despite being first reported in 1935, with subsequent important advances beginning in the 1970's, the development of this powerful reaction into a reliable methodology was somewhat limited. In recent years, there have been a number of reports from sever...

Formal (3+3) cycloaddition of silyl enol ethers catalyzed by trifric imide: domino Michael addition-claisen condensation accompanied with isomerization of silyl enol ethers.

We describe here a Tf₂NH-catalyzed formal (3+3) cycloaddition of silyl enol ethers with acrylates as a new domino reaction. In the domino sequence, the catalyst activates Michael addition, deprotonation of the resulting silyloxonium cation and intramolecular Claisen condensation. It was found that reaction modes significantly depend on the reaction temperature. We also examined the mechanistic ...

Chemo-, regio- and stereoselective preparation of silyl enol ethers from thiol esters and bis(iodozincio)alkane.

Treatment of thiol ester with bis(iodozincio)alkane in the presence of palladium catalyst followed by silylation affords Z-silyl enol ether chemo-, regio- and stereoselectively.