Recently, invited by renowned international academic journal Accounts of Chemical Research, Prof. Shi Feng from School of Chemistry & Materials Science at Jiangsu Normal University published aresearch paper, titling “Organocatalytic Asymmetric Synthesis of Indole-Based Chiral Heterocycles: Strategies, Reactions and Outreach” (DOI：10.1021/acs.accounts.9b00549). Now, the paper has been released online, and chosen as the paper of inside cover. This paper concludes important progresses that research team of Prof. Shi have made inrecent years. At the same time, this paper points out present problems and futuredevelopment of this field.
Associate Prof. Zhang Yuchen from School of Chemistry & Materials Science at Jiangsu Normal University is the firstauthor of this paper while postgraduate student Jiangsu the second author, Prof. Shi correspondent author.
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“Indole-based chiral heterocyclesconstitute a class of important heterocyclic compounds that are found innumerous pharmaceuticals, functional materials, and chiral catalysts orligands. Catalytic asymmetric synthesis, for which the 2001 Nobel Prize in Chemistry was awarded, has been demonstrated to be the most efficient methodfor accessing chiral compounds. Therefore, the catalytic asymmetric synthesisof indole-based chiral heterocycles has attracted great interest from the scientific community. However, the strategies toward this goal are ratherlimited, and great challenges remain in this field, such as metal contaminationin the products, the limited number of platform molecules with versatile reactivity, and the limited number of catalytic asymmetric reactions that offer high step economy, atom economy, and excellent enantiocontrol. Therefore, novel strategies for the catalytic asymmetric synthesis of indole-based chiralheterocycles are urgently needed.
To achieve this goal, our group has developed a series of unique strategies, such as designing and developing versatile platform molecules and their corresponding organocatalytic asymmetric reactions to access indole-based chiral heterocycles. In this Account, we describeour efforts to address the remaining challenges in this research field. Namely, we have designed and developed vinylindoles, indolylmethanols, arylindoles andindole derivatives as versatile platform molecules for the construction ofindole-based chiral heterocyclic scaffolds with structural diversity andcomplexity. Based on the reactivities of these platform molecules, we havedesigned and accomplished a series of organocatalytic asymmetric cycloaddition, cyclization, addition and dearomatization reactions with a high step economy, atom economy and excellent enantiocontrol.
Using these strategies, a wide range ofindole-based chiral heterocycles, including five-membered to seven-memberedheterocycles, axially chiral heterocycles and tetrasubstituted heterocycles,have been synthesized with high efficiency and excellent enantioselectivity. Inaddition, we have investigated the properties of some indole-based chiralheterocycles, including their bioactivities and catalytic activities, and showed that these chiral heterocycles have potent anticancer activities and promising catalytic activities in asymmetric catalysis. These results help elucidate the potential applications of indole-based chiral heterocycles indrug development and chiral catalysts.
The organocatalytic asymmetric synthesis of indole-based chiral heterocycles has undoubtedly become and will continue to bea hot topic in the field of asymmetric catalysis and synthesis. Our efforts, summarized in this Account, will not only open a window for the future development of innovative strategies toward organocatalytic asymmetric synthesis of indole-based chiral heterocycles but also inspire chemists worldwide to confront the remaining challenges in this field and prompt further advances.”
This paper doesn’t only point out a new direction for this field, but also encourages scientists all over the world to make joint effort to solve the challenging problems. This paper will further improve JSNU’s international influence.