Chiral Aziridine Phosphines as Highly Effective Promoters of Asymmetric Rauhut-Currier Reaction

A series of chiral enantiomerically pure aziridines containing a phosphine moiety were synthesized and successfully applied as organocatalysts in asymmetric intramolecular Rauhut-Currier reactions of p-quinone derivatives. The desired chiral phenols were achieved in high chemical yields and with satisfactory values of enantiomeric excess (up to 98% ee, in some cases). The stereochemical course of the title reaction may be controlled by the use of an appropriate enantiomer of the catalyst. The individual enantiomers of the organocatalyst led to the formation of specific enantiomers of the chiral product.

Automated summary

A series of chiral aziridines with a phosphine moiety were synthesized and used as organocatalysts in the asymmetric intramolecular Rauhut-Currier reactions of p-quinone derivatives. The desired chiral phenols were obtained with high yields and satisfactory enantiomeric excess values.