Cofactor-Controlled Chirality of Tropoisomeric Ligand
2016 (English)In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 35, no 11, 1956-1963 p.Article in journal (Refereed) PublishedText
A new tropos ligand with an integrated anion receptor receptor site has been prepared. Chiral carboxylate and phosphate anions that bind in the anion receptor unit proved capable of stabilizing chiral conformations of the achiral flexible bidentate biaryl phosphite ligand, as shown by variable temperature H-1 and P-31 NMR spectroscopical studies of palladium(0) olefin complexes. Palladium allyl complexes of the supramolecular ligand-chiral cofactor assemblies catalyzed asymmetric allylic substitutions of rac-(E)-1,3-diphenyl-2-propenyl carbonate and rac-3-cyclohexenyl carbonate with malonate and benzylamine as nucleophiles to provide nonracemic products. Although moderate enantioselectivities were observed, (ee:s up to 66%), the results confirm the ability of the anionic guests to affect the conformation of the ligand.
Place, publisher, year, edition, pages
American Chemical Society (ACS), 2016. Vol. 35, no 11, 1956-1963 p.
Carboxylation, Conformations, Ions, Negative ions, Palladium compounds, Substitution reactions, Allylic substitution, Anion receptor, Benzylamines, Chiral conformations, Olefin complexes, Palladium allyl complexes, Phosphate anions, Phosphite ligands
IdentifiersURN: urn:nbn:se:kth:diva-189668DOI: 10.1021/acs.organomet.6b00265ISI: 000377925600042ScopusID: 2-s2.0-84974712815OAI: oai:DiVA.org:kth-189668DiVA: diva2:949060
QC 201607142016-07-152016-07-112016-07-15Bibliographically approved