Novel Chiral 1,3-Diamines by a highly-modular Umpolung Strategy employing a Diastereoselective Fluorination – Nucleophilic Aromatic Substitution Sequence (Articolo in rivista)

Type

• Prodotto della ricerca (Classe)
• Articolo in rivista (Classe)

Label

• Novel Chiral 1,3-Diamines by a highly-modular Umpolung Strategy employing a Diastereoselective Fluorination – Nucleophilic Aromatic Substitution Sequence (Articolo in rivista) (literal)

Anno

• 2008-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1002/ejoc.200700764 (literal)

Alternative label

• Braun W., Calmuschi-Cula B., Englert U., Hoefner K., Alberico E., Salzer A. (2008)
  Novel Chiral 1,3-Diamines by a highly-modular Umpolung Strategy employing a Diastereoselective Fluorination – Nucleophilic Aromatic Substitution Sequence
  in European journal of organic chemistry (Print)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Braun W., Calmuschi-Cula B., Englert U., Hoefner K., Alberico E., Salzer A. (literal)

Pagina inizio

• 2065 (literal)

Pagina fine

• 2074 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url

• http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200700764/abstract (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 12 (literal)

Rivista

• European journal of organic chemistry (Rivista)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• Braun W., Calmuschi-Cula B., Englert U., Hoefner K., Salzer A.: Rhein Westfal TH Aachen Univ, Inst Anorgan Chem, D-52056 Aachen, Germany Alberico E.: CNR, Ist Chim Biomol, I-07040 Sassari, Italy (literal)

Titolo

• Novel Chiral 1,3-Diamines by a highly-modular Umpolung Strategy employing a Diastereoselective Fluorination – Nucleophilic Aromatic Substitution Sequence (literal)

Abstract

• A new highly modular synthesis for the rare class of chiral 1,3-diamines has been devised. It is accessible through nucleophilic aromatic ipso-substitution of fluorine in [(R,R)-1-fluoro-2-{(1-dimethylamino)ethyl}benzene]tricarbonylchromium and related complexes by secondary as well as primary amines. The precursor is accessible by a new diastereoselective electrophilic fluorination using N-fluorobenzenesulfonimide (NFSI), and the method is of potential interest for the synthesis of fluorinated pharmaceuticals. The protocol allows for the straightforward, modular synthesis of a broad library of diamines. A stock of 21 diamines has been synthesized. Primary amines bearing a stereogenic ?-center can be introduced without loss of optical purity, yielding planar-chiral diamines with two stereogenic centers in close proximity. An extended number of X-ray structures of these diamines is presented and discussed along with NMR experiments which show them to be \"chiral proton-donors\". The 1,3-diaminoarene moiety can easily be liberated from the chromium complex by decomplexation with I2 as exemplified in four examples. The new methodology adds a powerful tool to the synthesis of organic diamines, and opens a new way to the formerly difficult-to-access class of chiral 1,3-diamines. (literal)

Prodotto di

• Integrazione tra metabolomica e sintesi organica: prospettive verso la determinazione del riconoscimento molecolare (PM.P01.011.003) (Modulo)
• Istituto di chimica biomolecolare (ICB) (Istituto)
• Catalizzatori ad alta selettività in reazioni di idroformilazione ed idrogenazione (PM.P03.002.005) (Modulo)

Autore CNR

• ELISABETTA ALBERICO (Unità di personale interno)

Incoming links:

Autore CNR di

• ELISABETTA ALBERICO (Unità di personale interno)

Prodotto

• Istituto di chimica biomolecolare (ICB) (Istituto)
• Integrazione tra metabolomica e sintesi organica: prospettive verso la determinazione del riconoscimento molecolare (PM.P01.011.003) (Modulo)
• Catalizzatori ad alta selettività in reazioni di idroformilazione ed idrogenazione (PM.P03.002.005) (Modulo)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• European journal of organic chemistry (Rivista)