Synthesis of new chiral pyridines and efforts of their application to catalytic C(SP3)-H bond functionalization

2017 Fiscal Year Final Research Report

• Project/Area Number: 15K21046
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry; Chemical pharmacy
• Research Institution: Shizuoka University
• Principal Investigator: Sengoku Tetsuya 静岡大学, 工学部, 准教授 (70451680)
• Research Collaborator: YODA Hidemi 静岡大学, 工学部, 教授 (20201072) ; TAKAHASHI Masaki 静岡大学, 工学部, 教授 (30313935)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: テトラミン酸 / ピリジン誘導体 / 光学活性 / ビピリジン

Outline of Final Research Achievements

We have developed new synthetic methodology for enantiopure C2-symmetric and unsymmetric lactam-fused pyridines. A key outcome of this work is citric acid-promoted cyclisation of benzylidene tetramic acids and various enamines, leading to the relevant pyridines in enantiomerically pure forms. Additionally, we have been investigating their application in catalytic C(sp3)-H bond functionalization. Chiral bipyidine reagent was found to promote palladium-catalyzed reaction to give the product in excellent yield, albeit with low enantioselectivity.

Free Research Field

有機化学