Advanced Molecular Transformations by Development of Chiral Organosuperbase Catalysts

2015 Fiscal Year Final Research Report

• Project/Area Number: 24350045
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Partial Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Tohoku University
• Principal Investigator: TERADA Masahiro 東北大学, 理学(系)研究科(研究院), 教授 (50217428)
• Project Period (FY): 2012-04-01 – 2016-03-31
• Keywords: 不斉合成 / 有機分子触媒 / 水素結合 / 塩基 / 触媒 / 分子認識 / 物質変換 / 反応場

Outline of Final Research Achievements

The development of much stronger organobase is highly demanded to overcome intrinsic limitation of applicable pro-nucleophiles which have relatively acidic proton at the alpha-position, such as 1,3-dicarbonyl compounds and nitroalkanes. In general, the basicity of the organobases increases with increasing the resonance stability of their conjugate acids, the protonated form of the organobases. For instance, introduction of phosphazene or guanidine subunit(s) to the iminophosphorane core stabilizes its conjugate acid, aminophosphonium cation, to afford a series of phosphazene organosuperbases. However, the iminophosphorane modified by the additional phosphazene or guanidine subunit has never been applied to develop chiral organosuperbase so far. We hence designed a pseudo C2-symmetric P3-phosphazen and bis(guanidino)iminophosphorane as a novel family of chiral phosphazene organosuperbases and successfully developed these molecules.

Free Research Field

有機化学