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Asymmetric synthesis of binaphthyls through photocatalytic cross-coupling and organocatalytic kinetic resolution
Science China Chemistry ( IF 10.4 ) Pub Date : 2022-05-18 , DOI: 10.1007/s11426-022-1246-8
Heng-Hui Li , Jia-Yan Zhang , Shaoyu Li , Yong-Bin Wang , Jun Kee Cheng , Shao-Hua Xiang , Bin Tan

By capitalizing on the capability of photoredox catalysis to generate reactive radical intermediate under mild conditions, we established a photocatalytic cross-coupling protocol that could deliver both derivatives from 1-bromo-2-naphthols in combination with 2-naphthols or 2-naphthylamines. This distinct activation mode could overcome structural or electronic limitation associated with conventional coupling pathways. Additionally, a novel kinetic resolution protocol of unprotected BINOLs has been established with azodicarboxylates via chiral phosphoric acid (CPA) catalysis. Selectivity factor of up to 175 could be achieved and delivered to both enantiomers in atropisomerically enriched form after a simple work-up.



中文翻译:

通过光催化交叉偶联和有机催化动力学拆分不对称合成联萘

通过利用光氧化还原催化在温和条件下产生反应性自由基中间体的能力,我们建立了一种光催化交叉偶联方案,该方案可以提供 1-溴-2-萘酚与 2-萘酚或 2-萘胺的两种衍生物。这种独特的激活模式可以克服与传统耦合途径相关的结构或电子限制。此外,通过手性磷酸 (CPA) 催化,用偶氮二羧酸盐建立了一种新的无保护 BINOL 动力学拆分方案。经过简单的处理后,可以实现高达 175 的选择性因子,并以富含阻转异构体的形式将两种对映体传递给两种对映体。

更新日期:2022-05-22
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