Prolinol as a Chiral Auxiliary in Organophosphorus Chemistry

Several strategies for the development of the synthesis of P-chiral organophosphorus compounds with (L)-prolinol as a source of chirality have been examined. A reaction of L-prolinol with a set of different alkyl/arylphosphonous acid diamides led in most of the cases to the quantitative formation of the appropriate bicyclic oxazaphospholidines with complete diastereo and enantioselectivity. The latter were reacted with BH3 complex and the formed borane analogues were submitted to structural modifications leading to tertiary phosphine-boranes. Additionally, the effectiveness of oxazaphospholidines as ligands in transition metal asymmetric catalysis has been tested in hydrogenation of dehydroaminoacid esters and imine.

Automated summary

This study examines several strategies for the development of the synthesis of P-chiral organophosphorus compounds with (L)-prolinol as a source of chirality, and found that the resulting oxazaphospholidines show high effectiveness as ligands in transition metal asymmetric catalysis.