Tetrathiaheterohelicene Phosphanes as Helical-Shaped Chiral Ligands for Catalysis (Articolo in rivista)

Type
Label
  • Tetrathiaheterohelicene Phosphanes as Helical-Shaped Chiral Ligands for Catalysis (Articolo in rivista) (literal)
Anno
  • 2011-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/ejoc.201100726 (literal)
Alternative label
  • Monteforte, Marco; Cauteruccio, Silvia; Maiorana, Stefano; Benincori, Tiziana; Forni, Alessandra; Raimondi, Laura; Graiff, Claudia; Tiripicchio, Antonio; Stephenson, G. Richard; Licandro, Emanuela (2011)
    Tetrathiaheterohelicene Phosphanes as Helical-Shaped Chiral Ligands for Catalysis
    in European journal of organic chemistry (Print); Wiley-VCH-Verl.., -Weinheim (Germania)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Monteforte, Marco; Cauteruccio, Silvia; Maiorana, Stefano; Benincori, Tiziana; Forni, Alessandra; Raimondi, Laura; Graiff, Claudia; Tiripicchio, Antonio; Stephenson, G. Richard; Licandro, Emanuela (literal)
Pagina inizio
  • 5649 (literal)
Pagina fine
  • 5658 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://www.wiley-vch.de/publish/en/journals/bySubject/2046/ (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 10 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 28 (literal)
Note
  • ISI Web of Science (WoS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • University of Milan; Biolife Italiana Srl; University of Insubria; CNR-ISTM; Dipartimento Chim Organ & Ind; University of Parma; University of East Anglia (literal)
Titolo
  • Tetrathiaheterohelicene Phosphanes as Helical-Shaped Chiral Ligands for Catalysis (literal)
Abstract
  • Tetrathia[7]helicene-based phosphanes thiaheliphos (2a), nPr-thiaheliphos (2b) and di-nPr-thiaheliphos (2c) have been prepared from the 2,13-dilithio derivatives of thiahelicenes 1a-c by reaction with an excess of Ph2PCl. Protection of the air-sensitive products as BH3 adducts, from which the phosphanes 2a-c are easily regenerated on heating with ethanol, is described. New rhodium(I) complexes 8 and 9 were obtained by reaction of 2c with [Rh(COD)(2)](+)[BF4] and [BARF], respectively, which were converted by oxidation into the chelating phosphane-phosphane oxide Rh-I complexes 10 and 11. The monophosphane 5 was similarly prepared, and reaction of the dilithio species with ClP(O)(OEt)(2) gave the diphosphonate 17, which was characterized by X-ray crystallography. Comparison of data from DFT calculations (B3LYP/SVP) on 2c, 8 and 10 and X-ray data for 17 reveals a strong tension within the thiaheliphos ligands that is partially relaxed by increasing the Rh-P distances and the bite angle of the chelating ligand. Compound (P)-(+)-1c, obtained by chromatographic resolution, was transformed into optically pure (P)-(+)-2c, which was used in the asymmetric hydrogenation of itaconic acid ester and methyl 2-acetamidoacrylate (product ees up to 40%). (literal)
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