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 <i>p</i>-quinone derivatives. The desired chiral phenols were achieved in high chemical...
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MDPI AG
2022-08-01
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| Series: | Symmetry |
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| Online Access: | https://www.mdpi.com/2073-8994/14/8/1631 |
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| author | Aleksandra Buchcic-Szychowska Stanisław Leśniak Michał Rachwalski |
| author_facet | Aleksandra Buchcic-Szychowska Stanisław Leśniak Michał Rachwalski |
| author_sort | Aleksandra Buchcic-Szychowska |
| collection | DOAJ |
| description | 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 <i>p</i>-quinone derivatives. The desired chiral phenols were achieved in high chemical yields and with satisfactory values of enantiomeric excess (up to 98% <i>ee</i>, 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. |
| first_indexed | 2024-03-09T03:46:30Z |
| format | Article |
| id | doaj.art-7963362653f24be0b6ed12fec4731b9f |
| institution | Directory Open Access Journal |
| issn | 2073-8994 |
| language | English |
| last_indexed | 2024-03-09T03:46:30Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Symmetry |
| spelling | doaj.art-7963362653f24be0b6ed12fec4731b9f2023-12-03T14:33:18ZengMDPI AGSymmetry2073-89942022-08-01148163110.3390/sym14081631Chiral Aziridine Phosphines as Highly Effective Promoters of Asymmetric Rauhut–Currier ReactionAleksandra Buchcic-Szychowska0Stanisław Leśniak1Michał Rachwalski2Department or Organic and Applied Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, PolandDepartment or Organic and Applied Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, PolandDepartment or Organic and Applied Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, PolandA series of chiral enantiomerically pure aziridines containing a phosphine moiety were synthesized and successfully applied as organocatalysts in asymmetric intramolecular Rauhut–Currier reactions of <i>p</i>-quinone derivatives. The desired chiral phenols were achieved in high chemical yields and with satisfactory values of enantiomeric excess (up to 98% <i>ee</i>, 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.https://www.mdpi.com/2073-8994/14/8/1631asymmetric organocatalysisaziridinesphosphinesRauhut–Currier reactionstereoselectivity |
| spellingShingle | Aleksandra Buchcic-Szychowska Stanisław Leśniak Michał Rachwalski Chiral Aziridine Phosphines as Highly Effective Promoters of Asymmetric Rauhut–Currier Reaction Symmetry asymmetric organocatalysis aziridines phosphines Rauhut–Currier reaction stereoselectivity |
| title | Chiral Aziridine Phosphines as Highly Effective Promoters of Asymmetric Rauhut–Currier Reaction |
| title_full | Chiral Aziridine Phosphines as Highly Effective Promoters of Asymmetric Rauhut–Currier Reaction |
| title_fullStr | Chiral Aziridine Phosphines as Highly Effective Promoters of Asymmetric Rauhut–Currier Reaction |
| title_full_unstemmed | Chiral Aziridine Phosphines as Highly Effective Promoters of Asymmetric Rauhut–Currier Reaction |
| title_short | Chiral Aziridine Phosphines as Highly Effective Promoters of Asymmetric Rauhut–Currier Reaction |
| title_sort | chiral aziridine phosphines as highly effective promoters of asymmetric rauhut currier reaction |
| topic | asymmetric organocatalysis aziridines phosphines Rauhut–Currier reaction stereoselectivity |
| url | https://www.mdpi.com/2073-8994/14/8/1631 |
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