Development of Chiral Phosphoric Acids based on Ferrocene‐Bridged Paracyclophane Frameworks. Issue 18 (5th December 2013)

• Record Type: Journal Article
• Authors: Stemper, Jérémy; Isaac, Kévin; Pastor, Julien; Frison, Gilles; Retailleau, Pascal; Voituriez, Arnaud; Betzer, Jean‐François; Marinetti, Angela
• Is Part Of: Advanced synthesis & catalysis. Volume 355:Issue 18(2013)
• Page Start: 3613
• Page End: 3624
• Publication Date: 2013-12-05
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201300697
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>This work deals with the development of a new family of planar chiral phosphoric acids based on a ferrocenophane/paracyclophane scaffold. The synthetic approach has been improved by taking advantage of a chiral phosphorylating agent to access enantiomerically enriched acids <italic>via</italic> diastereomers separation. These phosphoric acids have been used as catalysts for the enantioselective H‐transfer reduction of α‐substituted quinolines with Hantzsch esters. Optimization of both the catalyst and the Hantzsch reductant allowed <italic>ee</italic> values in the range 82–92% to be attained starting from α‐arylquinolines.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4t37w9kf" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>