Heck Reaction of Amino Acid Derived Vinyl Substrates in the Synthesis of Homotyrosinol Derivatives

Abstract

An avenue to homotyrosinol derivatives through a Heck coupling of 4-iodophenyl acetate with a vinylglycinol derivative required extensive screening of catalysts and conditions. The use of Pd(OAc)₂ and N-phenylurea as the ligand ultimately provided excellent results.

Key words

coupling - Heck reaction - homotyrosine - palladium - N-phenylurea

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There was no reaction in THF at temperatures below 60 ˚C. At reflux, the substrate was converted into complex mixtures of products.