Stereodefined unsymmetrically 3, 3-disubstituted alkyl 2-bromopropenoates, 5, were regioselectively prepared by Pd-mediated reactions between 3-alkyl, 3-aryl and 3- alkoxycarbonyl substituted (E)-2, 3-dibromopropenoates,(E)-7, and aryl or 1-alkynylzinc chlorides. The stereospecificity of these reactions was found to be dependent on the type of substituent present in the 3-position of (E)-7. The (E)-stereochemistry of compounds 5b, ...
[Trost, Barry M.; Wrobleski, Stephen T.; Chisholm, John D.; Harrington, Paul E.; Jung, Michael Journal of the American Chemical Society, 2005 , vol. 127, # 39 p. 13589 - 13597]