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Journal Articles Advanced Synthesis and Catalysis Year : 2013

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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Dates and versions

hal-00872550 , version 1 (14-10-2013)

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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, 2013, 355, pp.3613-3624. ⟨10.1002/adsc.201300697⟩. ⟨hal-00872550⟩
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