Goldberg Active Template Synthesis of a [2]Rotaxane Ligand for Asymmetric Transition-Metal Catalysis

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• 作者：Steven Hoekman ; Matthew O. Kitching ; David A. Leigh ; Marcus Papmeyer ; Diederik Roke
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：June 24, 2015
• 年：2015
• 卷：137
• 期：24
• 页码：7656-7659
• 全文大小：334K
• ISSN：1520-5126

文摘

We report on the active template synthesis of a [2]rotaxane through a Goldberg copper-catalyzed C鈥揘 bond forming reaction. A C₂-symmetric cyclohexyldiamine macrocycle directs the assembly of the rotaxane, which can subsequently serve as a ligand for enantioselective nickel-catalyzed conjugate addition reactions. Rotaxanes are a previously unexplored ligand architecture for asymmetric catalysis. We find that the rotaxane gives improved enantioselectivity compared to a noninterlocked ligand, at the expense of longer reaction times.