Highly Novel Diastereoselective Synthesis of (E)-1-Aryl-1-alkenes

Abstract

A convenient, novel synthesis of (E)-1-phenyl-1-alkenes based on (Z)-1-bromo-1-alkenylboronate esters will be developed. α-Bromo-(Z)-1-alkenylboronate esters readily available from literature procedures will undergo a reaction with phenyllithium in tetrahydrofuran to provide the corresponding “ate” complexes. These “ate” complexes will then undergo intramolecular nucleophilic substitution reactions to provide the corresponding (E)-1-alkenylboronate esters containing a phenyl moiety which upon protonolysis with acetic acid will afford the corresponding (E)-1-phenyl-1-alkenes. All (E)-1-phenyl-1-alkenes were characterized by PMR and CMR spectral data successfully.