Study on the Origin of Chirality of Chiral Compounds by Using Asymmetric Autocatalysis

2017 Fiscal Year Final Research Report

• Project/Area Number: 15H03781
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Tokyo University of Science
• Principal Investigator: Soai Kenso 東京理科大学, 理学部第一部応用化学科, 教授 (90147504)
• Co-Investigator(Kenkyū-buntansha): 松本 有正 奈良女子大学, 自然科学系, 助教 (20633407) ; 川崎 常臣 東京理科大学, 理学部第一部応用化学科, 准教授 (40385513)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: 不斉自己触媒反応 / 不斉の起源 / そ合反応 / キラリティー / 不斉増幅 / 同位体 / 石膏 / 不斉触媒

Outline of Final Research Achievements

Asymmetric autocatalysis of pyrimidyl alkanol between diisopropylzinc and pyrimidine-5-carbaldehyde is a reaction in which chiral product acts as a chiral catalyst for its own production with amplification of enantiomeric excess (Soai reaction). The origin of chirality of chiral compounds has attracted much attention. We examined the origin of homochirality by using asymmetric autocatalysis. We found the enantiotopic face of achiral inorganic gypsum, nitrogen isotope (15N/14N) chiral diamine, chiral retgersite mineral, and chiral mesoporous silica act as chiral triggers of asymmetric autocatalysis to afford enantioenriched pyrimidyl alkanols with the corresponding absolute configurations with those of chiral triggers. We also elucidated the catalyst structure of asymmetric autocatalysis. We found that the change of temperature reverses of the sense of enantioselectivity of asymmetric autocatalysis using aromatic alkanols and amines as chiral triggers.

Free Research Field

有機合成化学，キラル化学，有機化学