Iron-Catalyzed Enantioselective Cross-Coupling Reaction

2014 Fiscal Year Final Research Report

• Project/Area Number: 26620085
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Kyoto University
• Principal Investigator: NAKAMURA Masaharu 京都大学, 化学研究所, 教授 (00282723)
• Project Period (FY): 2014-04-01 – 2015-03-31
• Keywords: 触媒的不斉合成 / 炭素ー炭素結合生成 / クロスカップリング反応 / 鉄触媒 / キラルホスフィン配位子 / 医薬品

Outline of Final Research Achievements

Transition metal catalyzed enantioselective cross-coupling reactions of organic halides with organometallics are powerful tool in asymmetric synthesis of chiral functional organic molecules. In combination with chiral ligands of appropriate choice, palladium and nickel catalysts have proved particularly useful. On the other hand, the most synthetically attractive transition metal, iron, have not yet been utilized as catalyst in the asymmetric cross-coupling reaction despite the remarkable progress of the iron-catalyzed cross-coupling reactions in the last decade. We have developed the first iron-catalyzed asymmetric cross-coupling reactions of α-haloalkanoates with ArMgBr using a catalytic amount of an iron salt and a chiral bisphosphine ligand, BenzP*, giving the products in high yields with good enantioselectivities. The developed asymmetric coupling offers and practical access to various chiral α-arylalkanoic acids derivatives, which are of significant pharmaceutical importance.

Free Research Field

有機化学