Alkylidenation of Ester Carbonyl Groups by means of a Reagent Derived from RCHBr2, Zn, TiCl4, and TMEDA. Stereoselective Preparation of (Z)-Alkenyl Ethers

Article abstract of DOI:10.1021/jo00228a055

Reagents prepared by reduction of 1,1-dibromoalkanes (R³CHBr2) with zinc and TiCl4 in the presence of N,N,N',N'-tetramethylethylenediamine in THF are effective in the conversion of esters (R¹CO2R²) to the corresponding alkenyl ethers (R¹(R²O)C=CHR³) with high Z selectivity.