Stereospecific preparation of ethyl (E) and (Z)-3-aryl-3-phenylpropenoates by Heck reaction

Marcial Moreno-Mañas, Montserrat Pérez, Roser Pleixats

Research output: Contribution to journalArticleResearchpeer-review

76 Citations (Scopus)


Ethyl cinnamate reacts with several para-substituted aryl iodides under Jeffery-Larock conditions (Pd(OAc)2, NaHCO3, n-Bu4NBr, DMF, Δ) to give ethyl (E)-3-aryl-3-phenylpropenoates as major compounds. The reaction of para-substituted ethyl cinnamates with iodobenzene under analogous conditions affords the corresponding Z isomers. The initially stereodefined alkene formed under Heck conditions undergoes a slow isomerization.
Original languageEnglish
Pages (from-to)7449-7452
JournalTetrahedron Letters
Issue number41
Publication statusPublished - 7 Oct 1996


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