ChemInform Abstract: Gosteli—Claisen Rearrangement of Propargyl Vinyl Ethers: Cascading Molecular Rearrangements.

Abstract

Gosteli-Claisen Rearrangement of Propargyl Vinyl Ethers: Cascading Molecular Rearrangements. -2-Alkoxycarbonyl-substituted propargyl vinyl ethers are used as substrates for the unprecedented rearrangements. They lead to cyclopentene and cyclobutane derivatives and furans along with the expected α-ketoesters (II), depending on the reaction conditions. The reaction proceeding in the presence of HFIP (III) requires dry conditions since water prevents the cycloalkene formation. Gold--catalyzed Gosteli-Claisen rearrangement is superior to the reaction carried out using TfOH as a catalyst. In the case of (Ie) small amount of (IX) is obtained. -(GILLE, A.; REHBEIN, J.; HIERSEMANN*, M.; Org. Lett. 13 (2011) 8, 2122-2125, http://dx.