Abstract
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Morita–Baylis–Hillman-like tri- and tetra-substituted β-iodoalkene adducts can be efficiently synthesized from activated alkynes and aldehydes utilizing MgI2 in CH2Cl2 in excellent yields (65–96%, 16 examples) under mild reaction conditions. A variety of electronically diverse aldehydes react with several electron-deficient alkynes in this manner. The reactions proceed in 2–16h room temperature or reflux. Furthermore, a trisubstituted Z-alkene was shown to thermodynamically isomerize upon exposure to MgI2 and heat to obtain the corresponding (E)-alkene adduct as the only observed stereoisomer.