Development of chiral phosphoric acids based on ferrocene-bridged paracyclophane frameworks

Abstract : 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 via diastereomers separation. These phosphoric acids have been used as catalysts for the enantioselective H-transfer reduction of alpha-substituted quinolines with Hantzsch esters. Optimization of both the catalyst and the Hantzsch reductant allowed ee in the range 82-92% to be attained starting from alpha-arylquinolines.
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Submitted on : Monday, October 14, 2013 - 12:31:14 AM
Last modification on : Tuesday, June 11, 2019 - 12:02:05 PM
Long-term archiving on : Friday, April 7, 2017 - 10:13:14 AM

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Jérémy Stemper, Kevin Isaac, Julien Pastor, Gilles Frison, Pascal Retailleau, et al.. Development of chiral phosphoric acids based on ferrocene-bridged paracyclophane frameworks. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2013, 355, pp.3613-3624. ⟨10.1002/adsc.201300697⟩. ⟨hal-00872550⟩

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