Related Experiment Video
Updated: Sep 3, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Redox-neutral synthesis of azepane-fused spiroindolenines via Sc(OTf)3-catalyzed cascade [1,5]-hydride
Liwen Zhang1, Jie Chen1, Guo Tang1
1State Key Laboratory of Southwestern Chinese Medicine Resources, College of Medical Technology, School of Pharmacy, Chengdu University of Traditional Chinese Medicine Chengdu 611137 China xinxie@cdutcm.edu.cn lixiang2@cdutcm.edu.cn.
Abstract:
Herein, we report the first Sc(OTf)3-catalyzed redox-neutral cascade [1,5]-hydride transfer/cyclization for the efficient synthesis of azepane-fused spiroindolenines. This structurally strained seven-membered-ring scaffold has long eluded efficient access. The reaction proceeds via Knoevenagel condensation, intramolecular hydride transfer, and cyclization, delivering the target products in good to excellent yields (up to 97%). Notably, this protocol eliminates the need for substrate pre-functionalization or external oxidants. The methodology is readily scalable to the gram scale and enables diverse downstream transformations, including late-stage coupling with zidovudine. Preliminary biological evaluation indicates that selected derivatives exhibit micromolar antiproliferative activity against ovarian cancer cells, warranting further investigation as potential anticancer agents.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
11:45Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Related Concept Videos
Cycloaddition Reactions: Overview
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation