Stereospecific protonative deconjugation of alkyl 3-trimethylstannylalk-2-enoates
Abstract
Treatment of the β-trimethylstannyl α,β-unsaturated esters (3)–(8) with lithium di-isopropylamide in tetrahydrofuran (THF)[(3)–(5)] or THF–hexamethylphosphoramide [(6)–(8)], followed, in each case, by transfer of the resultant solution to a cold (–98 °C) solution of acetic acid in ether, provides exclusively the alkyl 3-trimethylstannylalk-3-enoates (9)–(14), respectively.