The Matteson homologation with vinyl nucleophiles was found
to be an efficient and versatile protocol for the synthesis of
substituted chiral allyl alcohols in a highly stereoselective
fashion. These alcohols can be coupled with N-protected
glycine and subsequently subjected to zinc-chelated esterenolate Claisen rearrangements to yield highly substituted
unsaturated amino acids. By varying the nucleophiles used in
the Matteson homologations, the method allows control over
not only the stereogenic centers but also the side-chain
substitution pattern in the newly formed γ,δ-unsaturated amino
acids
