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.

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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
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article

Phosphonamidates of Camphorsultam: Versatile Building Blocks for the Synthesis of P‐Chiral Phosphorous(V) Compounds

A. Matsumoto, Hideyasu China, Kenji Watanabe, Junpei Matsuoka et al.
3 citations
Advanced Synthesis & Catalysis
Organophosphorus compounds synthesis
0.75
article

Phosphonamidates of Camphorsultam: Versatile Building Blocks for the Synthesis of P‐Chiral Phosphorous(V) Compounds

A. Matsumoto, Hideyasu China, Kenji Watanabe, Junpei Matsuoka, Akari Miyawaki, Mônica Masako Nakamoto, Yasutomo Yamamoto, S. Nakai, Minako Murata, Yurika Kambara, Tomoe Ishiura
article en
3 citations

Abstract

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.

Advanced Synthesis & CatalysisVol. 367(3)
Doshisha Women's College of Liberal Arts (JP), Kindai University (JP)
Openalex Percentile: Top 31%
Organophosphorus compounds synthesis
0.75
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