Development of Asymmetric Synthetic Method of Planar-Chiral Heterocycles Based on Their Dynamic Stereochemical Property

2015 Fiscal Year Final Research Report

• Project/Area Number: 26888012
• Research Category: Grant-in-Aid for Research Activity Start-up
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: Kyushu University
• Principal Investigator: Ano Yusuke 九州大学, 先導物質化学研究所, 学術研究員 (20736813)
• Project Period (FY): 2014-08-29 – 2016-03-31
• Keywords: 動的面不斉 / 不斉合成 / 中員環アミン

Outline of Final Research Achievements

In this study, design and synthesis of dynamic planar-chiral cyclic amines were carried out. The stereochemical analysis of newly obtained planar-chiral cyclic amines revealed that they can be racemized rapidly at room temperature. Control of their dynamic stereochemical behavior by using intramolecular hydrogen bond or coordination of metal complexes were also examined. In addition, stereospecific transformation methods of optically active planar-chiral cyclic amines to central chiral molecules were developed. For example, transannular reaction with strong base and epoxidation proceeded stereospecifically. Furthermore, enantioselective synthesis of planar chiral cyclic amines was accomplished based on the Pd-catalytzed asymmetric cyclization reaction.

Free Research Field

有機化学