Phosphonamidates of Camphorsultam: Versatile Building Blocks for the Synthesis of <i>P</i>‐Chiral Phosphorous(V) Compounds
Abstract Camphorsultam was utilized for the optical resolution of P ‐chiral phosphorous compounds. After chromatographic separation of diastereomeric R P ‐ and S P ‐phosphonamidate intermediates, subsequent substitution reactions with phenol derivatives yielded P ‐chiral phosphonic acid aryl esters with excellent enantioselectivities. In these processes, chiral sulfonamide of camphorsultam demonstrated superior abilities as an optical‐resolving agent and a good leaving group. This method was applied to the synthesis of P ‐chiral phosphinic esters, phosphonamidates, and thiophosphonate diesters.
Authors
- A. Matsumoto (ORCID: https://orcid.org/0000-0002-6388-2130)
- Hideyasu China
- Kenji Watanabe (ORCID: https://orcid.org/0000-0002-0463-4831)
- Junpei Matsuoka (ORCID: https://orcid.org/0000-0002-2648-0853)
- Akari Miyawaki
- Mônica Masako Nakamoto (ORCID: https://orcid.org/0000-0002-2947-5128)
- Yasutomo Yamamoto (ORCID: https://orcid.org/0000-0002-5959-1787)
- S. Nakai
- Minako Murata
- Yurika Kambara
- Tomoe Ishiura
Institutions
- Doshisha Women's College of Liberal Arts (JP)
- Kindai University (JP)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2024-11-26
- DOI
- https://doi.org/10.1002/adsc.202401268
- Citations
- 3
- Primary Topic
- Organophosphorus compounds synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.75