Asymmetric induction by the isotope chirality and cryptochirality for the highly sensitive chiral discrimination

2014 Fiscal Year Final Research Report

• Project/Area Number: 23685012
• Research Category: Grant-in-Aid for Young Scientists (A)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: University of Fukui (2012-2014); Tokyo University of Science (2011)
• Principal Investigator: KAWASAKI Tsuneomi 福井大学, 工学(系)研究科(研究院), 准教授 (40385513)
• Project Period (FY): 2011-04-01 – 2015-03-31
• Keywords: 同位体不斉 / 不斉自己触媒反応 / 不斉誘導 / クリプトキラリティー / キラル識別

Outline of Final Research Achievements

We have developed the highly sensitive method to recognize a small chirality by using asymmetric autocatalysis. It has been demonstrated that asymmetric autocatalysis could discriminate an extremely small difference between the enantiomers arising from oxygen-isotope substitution.
Moreover, chiral crystals of achiral nucleobase cytosine and adenine, and triester can be discriminated by asymmetric autocatalysis with amplification of ee. A chiral mineral, cinnabar, served as a chiral source of asymmetric autocatalysis to afford enantioenriched 5-pyrimidyl alkanol. The adsorption structures of related compounds were observed with atomic force microscopy.
The oriented prochirality, i.e., two-dimensional chirality at the surface of achiral single crystal could also be discriminated by asymmetric autocatalysis to afford enantioenriched alkanol with high ee. The absolute configuration of the alkanol correlated with the chirality at the crystal surface.

Free Research Field

不斉合成・キラル化学