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Organocatalytic Atroposelective Cross-Coupling of 1-Azonaphthalenes and 2-Naphthols |
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| Authors: | Bing-Chao Da Dr Yong-Bin Wang Dr Jun Kee Cheng Dr Shao-Hua Xiang Prof Dr Bin Tan |
| Institution: | 1. Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, 518055 Shenzhen, China;2. Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, 518055 Shenzhen, China
Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, 518055 Shenzhen, China |
| Abstract: | Atroposelective cross-coupling is one of the most appealing routes to construct axially chiral binaphthyl molecules due to the modular and succinct nature. Although transition-metal-catalyzed cross-couplings offer reliable synthetic means, alternative reaction modes that could be applied to broader substrate range without their pre-functionalization is highly desirable. Herein we show that the application of chiral Brønsted acid catalyst as organocatalyst could accomplish cross-coupling of 1-azonaphthalenes and 2-naphthols with high efficiency, exclusive C4-selectivity as well as excellent enantioselectivity and functional group compatibility. The identification of acylimidazolinone auxiliary for azo activating group, effective remote catalyst control and arene resonance effect synergistically play key roles in the development of this method. The utility is further demonstrated by transformations of the products into other binaphthyl compounds with perfectly retained axial chirality. |
| Keywords: | Atroposelectivity Control Axial Chirality CPA Catalysis Cross-Coupling Organocatalysis |