Wang Jing-Yi, Lin Jie, Zhang Chaoshen, Sun Jianwei
Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, 999077, Hong Kong SAR (China).
Angew Chem Int Ed Engl. 2025 Jul 21;64(30):e202507798. doi: 10.1002/anie.202507798. Epub 2025 Jun 1.
Disclosed here is a "one-pot self-assembly" strategy for the enantioselective synthesis of a spiro bisindole molecule directly from indole and acetone. This convenient synthesis contrasts drastically to the typical long sequence required for other privileged C-symmetric spirocycles. The use of an alcohol additive in cooperation with chiral phosphoric acid (CPA) catalysis proved crucial to the good efficiency and enantioselectivity. The favorable interaction between the additive and CPA was confirmed by nuclear magnetic resonance (NMR) and density functional theory (DFT) studies. The obtained enantiopure C-symmetric bisindole was demonstrated as a useful backbone of chiral catalysts/ligands.
本文公开了一种“一锅自组装”策略，可直接从吲哚和丙酮对映选择性合成螺双吲哚分子。这种简便的合成方法与其他具有特殊C对称性螺环所需的典型长序列形成了鲜明对比。事实证明，醇添加剂与手性磷酸（CPA）催化协同使用对于良好的效率和对映选择性至关重要。通过核磁共振（NMR）和密度泛函理论（DFT）研究证实了添加剂与CPA之间的良好相互作用。所获得的对映体纯C对称双吲哚被证明是手性催化剂/配体的有用骨架。
