Stereoselective synthesis of oxygenated trisubstituted olefins using N-ylides [2,3]rearrangement

Article abstract of DOI:10.1055/s-1998-1745

[2,3]Sigmatropic rearrangement of N-(ethoxycarbonyl)-methyl-β-methallylammonium ylide with an oxygen functionality at the β-position or γ-position forms trisubstituted trans-olefins with high stereoselectivity. On the other hand, the rearrangement of salts having a tiglyl ester moiety instead of a carbethoxy group affords cis-olefins. The present method was applied to the synthesis of plaunotol.