Chiral recognition of anions by P-chiral phosphoric triamides

2023 Fiscal Year Final Research Report

• Project/Area Number: 21K05032
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
• Research Institution: Yamagata University
• Principal Investigator: Kondo Shin-ichi 山形大学, 理学部, 教授 (20281503)
• Project Period (FY): 2021-04-01 – 2024-03-31
• Keywords: リン酸トリアミド / キラル / アニオン認識 / 不斉補助剤

Outline of Final Research Achievements

Chiral anion recognition has recently received attention. We studied chiral anion recognition by phosphorus triamides with P-chirality bearing three different substituents on the phosphorus atom. Phosphorus triamides bearing an L-amino acid with an amide linkage were prepared and the diastereomers were isolated by HPLC. The P-chiral center is shown to be stable at r.t. and the phosphorus triamides exhibit chiral recognition with anions. In addition, diastereomers of phosphorus triamides bearing a chiral amino acid derivative with ester linkage were also successfully isolated, followed by hydrolysis to give the enantiomers of chiral phosphorus triamides. This is the first example of synthesis and recognition properties of chiral phosphorus triamides.

Free Research Field

分子認識化学

Academic Significance and Societal Importance of the Research Achievements

本研究ではリン原子がキラル中心となる3つの異なる置換基を有するリン酸トリアミドの合成に成功し、P-キラルリン酸トリアミドがキラルアニオン認識を可能であることを実証した。P-キラルリン酸トリアミドの合成例はなく、初めての例である。キラル認識は薬物やファインケミカルなどの分野で重要であり、ここに新たな官能基を導入できたことは学術的な意味がある。今後、キラル有機触媒としての展開も期待できる。