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P-chirogenic organophosphorus compounds for asymmetric catalysis

Reference

04445-01

Patents status

French patent application FR1156686 filed on July 22th, 2011 and entitled « Composés organophosphorés p-chirogéniques »

Inventors

Sylvain JUGÉ
Jérôme BAYARDON
Emmanuelle RÉMOND
Hugo LAURÉANO
Jean-Christophe HENRY
Frédéric LEROUX
Françoise COLOBERT

commercial status

Exclusive or non-exclusive licenses

Laboratory

Description

CONTEXT

Asymmetric catalysis has been for the last decades in the fine chemical and pharmaceutical companies’ center of attention. Therefore numerous types of catalysts exist to do such synthesis knowing that a focus has been made specifically on organocatalyst and organometallic catalyst. Among theses compounds, P-chirogenic (chiral phosphorous) organophosphorus compounds are very interesting as ligands for organometallic catalysis or as simple organocatalysts. Nevertheless, these compounds are not often used due to difficulties of synthesis. 

TECHNICAL DESCRIPTION

In the present work, the inventors have developped a process for the synthesis of novel P-chirogenic organophosphorus from a phosphine borane and an aromatic compound. The patent application protects the leading compounds, its process as well as the intermediates.

DEVELOPMENT STAGE

  • Suitable process for multi-gram scale synthesis;
  • Asymmetric hydrogenation, allylation and C-C bond coupling catalyzed application has been successfully undertaken.

BENEFITS

The process apart from being easy to handle lead to a wide variety of products while no other previous methods could do so with a high enantiomeric excess.

INDUSTRIAL APPLICATIONS

As stated, the main application of this compounds revolves around asymmetric catalysis as organometallic catalyst ligands or as organocatalysts, especially for asymmetric hydrogenation or allylation. They may be also useful as agrochemical and therapeutic substances, or as reagents or intermediates for fine chemistry.

For further information, please contact us (Ref 04445-01)


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