Divergent Asymmetric Synthesis of Polycyclic Spiroindolines via Cascade Cycloadditions
Huan Zhang , Chenchen Ma , Fengfeng Yin , Yu Jiang , Jiaqi Du , Peifang Lu , Jianhua Wang , Jitian Liu , Xiaoxun Li
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (23) : 3157 -3164.
The asymmetric construction of polycyclic spiroindolines featuring one or more quaternary stereocenters remains a significant challenge in synthetic chemistry. We report a highly chemoselective and stereoselective cascade cycloadditions of newly designed oxazepino indolones with 5-methylene-1,3-dioxanones, employing an iridium catalyst in combination with the Carreira ligand for the divergent synthesis of chiral polycyclic spiroindolines. This strategy enables the construction of a series of pentacyclic spiroindolines featuring two chiral quaternary stereocenters and one tertiary stereocenter in good yields with excellent chemoselectivity and stereocontrol (30 examples, up to 81% yield, >20 : 1 dr, 99% ee). The process was scalable, and synthetic transformations of the products were performed to demonstrate their practical utility.
Polycyclic spiroindolines / Cascade cycloadditions / Divergent synthesis / Quaternary stereocenters / Stereoselectivities / Fused-ring systems / Asymmetric synthesis / Domino reactions
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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