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Phosphinates

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  • The reaction of h-phosphinates and secondary phosphine oxides with amines and alcohols proceeds highly stereo specifically to give the corresponding coupling products with inversion of configuration at the phosphorus center under the atherton-todd reaction conditions.

  • This finding leads to the establishment of a general and efficient method for the synthesis of a variety of optically active organo phosphorus acid derivatives from the easily available chiral h-phosphinates and secondary phosphine oxides.

  • Racemic acyl phosphinates and formyl phosphinate hydrate were used directly as the substrates in a proline derivative catalyzed cross aldol reaction with ketones.

  • Because of the preexisting the phosphorus stereogenic center, a mixture of two diastereomers of the corresponding a-hydroxy phosphinates were obtained in this reaction.

  • Good to high enantioselectivities (up to 99% ee) were obtained simultaneously for both of these two diastereomers in good yields.

  • Good diastereoselectivities were also obtained when the reaction generates an additional carbon stereogenic centera-Hydroxyphosphinic acid derivatives, such as a-hydroxy phosphinates, have been shown to be very important enzyme inhibitors.

  • Hydroxy phosphinate-derived peptides have been used as the inhibitors of human immunodeficiency virus (HIV) protease and renin also these compounds have found use as GABA antagonists herbicides.

  • With the exception of phosphinic acids, the phosphoryl group in other phosphinic acid derivatives, such as phosphinates, generally are chiral because the pentavalent phosphorus atom has a tetrahedral structure.

  • Enantiomers due to such phosphorus chirality may have totally different biological activities
    One enantiomer was found significantly more herbicidal than the other enantiomer or the racemic mixture.

  • This finding evinces the importance of the phosphorus chirality in the biological activity of the phosphinate compounds.

  • Thus, developing an asymmetric synthesis for a-hydroxy phoshinates that can fix both the stereo chemistry of the a-hydroxy-substituted carbon and the phosphorus stereogenic centers during the synthesis is very important.

  • Such a method is expected to have the potential of lowering production costs and use rates, reducing the side effects, and lessening the environmental burden during the manufacture and application of these materials.

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