Development of Novel Quaternary Phosphonium Salt Catalysts by the Use of Chiral Phosphine Library

2014 Fiscal Year Final Research Report

• Project/Area Number: 25870335
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry; Organic chemistry
• Research Institution: Nagasaki University (2014); Kyoto University (2013)
• Principal Investigator: SHIRAKAWA Seiji 長崎大学, 水産・環境科学総合研究科(環境), 准教授 (60459865)
• Project Period (FY): 2013-04-01 – 2015-03-31
• Keywords: 第四級ホスホニウム塩 / 不斉合成 / 有機分子触媒 / 相間移動触媒 / 精密有機合成 / 環境調和型反応 / グリーンケミストリー / 触媒ライブラリ

Outline of Final Research Achievements

During last two decades, a variety of chiral quaternary ammonium salts have been developed as reliable catalysts for asymmetric phase-transfer reactions. On the other hand, only a few examples of chiral quaternary phosphonium salts have been reported, and hence the development of new effective chiral quaternary phosphonium salts is an important challenge in organocatalytic chemistry. Our approach for the discovery of effective chiral quaternary phosphonium salts relies on the use of commercially available chiral phosphine compounds as catalyst precursors. This approach allows facile construction of a catalyst library of chiral quaternary phosphonium salts. The optimized catalyst has successfully been applied to highly enantioselective conjugate additions under base-free neutral phase-transfer conditions with low catalyst loading. Based on the catalyst design, we have also developed new bifunctional phosphonium salts for highly enantioselective phase-transfer reactions.

Free Research Field

有機合成化学