Catalytic Deamino-Diels–Alder and Formal [2+2+2] Annulation Enabled by Indolyl-Vinyl-Iminium as a C4 Synthon: Divergent Assembly of Indole Polycyclic Skeletons

Q: What does this research mean for the field?

Indolyl-vinyl-iminium functions as a novel C4 synthon that enables the divergent assembly of indole polycyclic skeletons through gold(I)-catalyzed cascade cyclizations. Novelty: ClaimNovelty.METHODOLOGICAL. Consensus alignment: ConsensusAlignment.NEUTRAL.

Shiyang Xin; Xiaopeng Qiu; Weiming Wang; Mengqi Wu; Yujia Bai; Haochen Zhang; Xueyu Yao; Huaying Liu; Zeshi Li; Yan Fu; Lu Yang; Kaitong Zhuang; Yining Zhang; Ruijuan Xing; Ran Guo; Zenghui Sun; Zhenhua Pan; Lei Wang

doi:10.1021/acs.orglett.6c03633

Key Points

To introduce indolyl-vinyl-iminium as a versatile C4 synthon for the divergent catalytic construction of structurally distinct indole polycyclic frameworks.
Applied gold(I) catalysis to induce intramolecular deamino-Diels–Alder cascade cyclizations.
Developed a sequential gold(I) and bistriflimide (HNTf2) co-catalyzed system for intermolecular formal [2+2+2] annulations.
Performed density functional theory calculations and controlled laboratory experiments to probe reaction mechanisms and stereochemical selectivity.
Successfully assembled diverse benzo[b]carbazole architectures via gold(I)-catalyzed intramolecular deamino-Diels–Alder cascades.
Synthesized a broad spectrum of hexahydroindolo[2,3-b]carbazole derivatives through sequential catalytic intermolecular [2+2+2] annulation.
Identified critical mechanistic transition states that dictate the high diastereoselectivity observed across the reaction pathways.

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Implication

Chemical synthesis study demonstrates catalytic cascade cyclizations using an indolyl-vinyl-iminium synthon, indicating a versatile route to complex indole polycyclic skeletons.

Abstract

Herein, we report indolyl-vinyl-iminium as a new C4 synthon. It enables the divergent assembly of indole polycyclic skeletons via cascade cyclizations, including a gold(I)-catalyzed intramolecular deamino-Diels–Alder reaction for the construction of benzo[b]carbazoles and a sequential gold(I)/HNTf2-catalyzed intermolecular formal [2+2+2] annulation that affords a broad spectrum of hexahydroindolo[2,3-b]carbazole derivatives. Theoretical calculations and control experiments shed light on the reaction mechanism and the origin of the diastereoselectivity.

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Cite This Study

Xin et al. (2026) studied this question.

synapsesocial.com/papers/6aa913a29013453be30a1aaa https://doi.org/10.1021/acs.orglett.6c03633

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Catalytic Deamino-Diels–Alder and Formal [2+2+2] Annulation Enabled by Indolyl-Vinyl-Iminium as a C4 Synthon: Divergent Assembly of Indole Polycyclic Skeletons

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Catalytic Deamino-Diels–Alder and Formal [2+2+2] Annulation Enabled by Indolyl-Vinyl-Iminium as a C4 Synthon: Divergent Assembly of Indole Polycyclic Skeletons

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