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Stereocontrolled One‐Step Synthesis of Difunctionalised Cispentacin Derivatives through Ring‐Opening Metathesis of Norbornene β‐Amino Acids

2015; Wiley; Volume: 2015; Issue: 6 Linguagem: Inglês

10.1002/ejoc.201403493

1434-193X

Lóránd Kiss, Márton Kardos, Enikő Forró, Ferenc Fülöp,

Asymmetric Synthesis and Catalysis

Abstract Through the ring‐opening metathesis of norbornene or oxanorbornene β‐amino acids with ethylene in the presence of certain Ru catalysts, a facile and convenient stereocontrolled one‐step method was devised for the preparation of divinylated cispentacins and oxacyclic cispentacin stereoisomers with four chiral centres. The products are interesting scaffolds for peptide chemistry and for the synthesis of novel functionalised materials through olefinic bond transformations. The ring‐opening metathesis proceeds without affecting the chiral centres of the starting molecules, so that their stereochemistry was conserved and determines the configuration of the chiral centres in the products.