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Stereocontrolled One‐Step Synthesis of Difunctionalised Cispentacin Derivatives through Ring‐Opening Metathesis of Norbornene β‐Amino Acids
Author(s) -
Kiss Loránd,
Kardos Márton,
Forró Enikő,
Fülöp Ferenc
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403493
Subject(s) - norbornene , chemistry , metathesis , ring (chemistry) , stereochemistry , catalysis , enantioselective synthesis , combinatorial chemistry , ethylene , salt metathesis reaction , molecule , amino acid , organic chemistry , polymerization , polymer , biochemistry
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.