Asymmetric Conjugate Addition of Phosphine Sulfides to α-Substituted β-Nitroacrylates Using Cinchona Alkaloid Amide Catalysts
Chiral phosphine-containing amino acids are useful motifs in pharmaceutical compounds. In this study, we developed the asymmetric conjugate addition of phosphine sulfides with α-substituted β-nitroacrylates to synthesize phosphine-containing amino acid precursors with chiral tetrasubstituted carbon centers. This method showed a wide substrate scope, and the obtained products were converted into various chiral compounds. The origin of the enantioselectivity was clarified by computational analysis.
Authors
- Kazuki Fujita
- Tsunayoshi Takehara (ORCID: https://orcid.org/0000-0002-4113-7578)
- Shuichi Nakamura (ORCID: https://orcid.org/0000-0001-5633-8367)
- Naoki Yasukawa (ORCID: https://orcid.org/0000-0002-7994-0470)
- Takeyuki Suzuki (ORCID: https://orcid.org/0000-0002-2137-0276)
- Akane Iwamura
- Kosei Miyake
Institutions
- Nagoya Institute of Technology (JP)
- The University of Osaka (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-20
- DOI
- https://doi.org/10.1021/acs.orglett.4c02643
- Citations
- 4
- Primary Topic
- Organophosphorus compounds synthesis
- Type
- article
- Field-Weighted Citation Impact
- 1.00