Design and Synthesis of Dynamic Planar Chiral Medium-sized Cyclic Molecule

2018 Fiscal Year Final Research Report

• Project/Area Number: 16H04113
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kyushu University
• Principal Investigator: Tomooka Katsuhiko 九州大学, 先導物質化学研究所, 教授 (70207629)
• Research Collaborator: Igawa Kazunobu ; Kawasaki Yuuya
• Project Period (FY): 2016-04-01 – 2019-03-31
• Keywords: 有機合成化学 / 分子キラリティー / 動的面不斉分子 / 機能性キラル分子 / 不斉合成

Outline of Final Research Achievements

We performed systematic study on dynamic planar chiral heterocycles: nine-membered E,Z-diallylic heterocycles and [7]-orthocyclphenes, and found that their stereochemical stabilities are highly dependent on substituent on the E-alkene, embedded heteroatom X in the ring, and ring size. Also we have found that stereochemical stability of the planar chiral molecules can be controlled by addition of Lewis acid. Furthermore, we have developed dynamic asymmetric induction method which provides enantioenriched forms of the planar chiral molecules.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

キラル分子の研究は化学の基礎や生命現象の本質を理解するために重要である．その主たる対象は炭素中心性不斉を有するキラル分子であった．これに対して本研究では，我々が先に見出した動的面不斉を有する中員環分子という新規なキラル分子を対象として系統的な研究を行い，その学理を探求した．また，その立体化学を外的キラル因子の影響で変化させて制御する動的不斉誘起法の開発に成功した．