Development of new tandem reactions by using bis(oxazoline) ligands

2014 Fiscal Year Final Research Report

• Project/Area Number: 24590026
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Toho University
• Principal Investigator: KATO Keisuke 東邦大学, 薬学部, 教授 (80276609)
• Co-Investigator(Kenkyū-buntansha): KUSAKABE Taichi 東邦大学, 薬学部, 講師 (00600032)
• Co-Investigator(Renkei-kenkyūsha): INOUYE Yoshio 東邦大学, 薬学部, 教授 (00136053) ; KANNO Yuichiro 東邦大学, 薬学部, 講師 (40453849)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: パラジウム / ビスオキサゾリン / カルボニル化 / CCC-coupling反応 / 5-メトキシ-3(2H)-フラノン / ジヘテロアリールケトン

Outline of Final Research Achievements

In our early work, we found that bis(oxazoline) (box) ligand enhances the π-electrophilicity of palladium (II). In this work, we were successful in developing cyclization-carbonylation-cyclization-coupling (CCC-coupling) reaction and an efficient synthetic method of 5-methoxy-3(2H)-furanones utilizing characteristic property of the box-Pd(II) complexes. The former reaction is useful for the synthesis of symmetrical ketones bearing two pharmaceutically important heterocycles, such as indoles, benzofurans, benzothiphenes, and quinolones. In the latter reaction, steroidal compounds bearing spirofuranone structure at C17 were obtained in good yield from alkyne substrates in one-step reactions.

Free Research Field

有機金属化学