报告题目: Exploring the Chemistry of Spiroindolenines by Mechanistically-Driven Reaction Development

报告人: 郑超副研究员，中国科学院上海有机所

时  间：2020年12月9日下午3：00-5：00

地  点：嘉锡楼413

报告简介:

The Pictet−Spengler reaction is a fundamental named reaction in organic chemistry, and it is the most straightforward method for the synthesis of tetrahydro-β-carbolines, a core structure embedded in numerous alkaloids. Spiroindolenines are often proposed as possible intermediates in Pictet−Spengler reactions. However, whether the spiroindolenine species is an intermediate in the mechanism of the asymmetric Pictet−Spengler reaction remains unclear. Previous studies regarding this issue have not reached a consensus. Systematic studies on the chemistry of spiroindolenines will advance the field of synthetic organic chemistry.

In the past several years, we have achieved a series of highly enantioselective synthesis and stereospecific ringexpansive migration of spiroindolenines. Comprehensive density functional theory (DFT) calculations and Born–Oppenheimer molecular dynamics (BOMD) simulations provided a uniform mechanistic understanding on Pictet–Spengler reactions, especially on the relationship between the electronic properties of the substrates and the stereochemistry of the reaction. Guided by the novel mechanistic knowledges, we discovered an array of unprecedented reaction patterns of spiroindolenines by rationally tuning the reactivity of the potential migratory group or regulating the multiple competitive reaction pathways. In this talk, we will present the results of our exploration on the chemistry of spiroindolenines and mechanistically-driven reaction development beyond classic Pictet–Spengler reaction.

报告人简介:

郑超，1985年出生于湖北省。2007年毕业于上海交通大学，获得学士学位。2012年毕业于中国科学院上海有机化学研究所，获得博士学位（导师：游书力研究员和李玉学研究员）。2012年起在上海有机化学研究所金属有机化国家重点实验室工作，2015年晋升为副研究员。目前主要从事不对称催化反应以及过渡金属催化反应的机理研究工作。作为第一作者或（共同）通讯作者发表论文24篇，参与编写英文专著4章，累计引用3500余次。曾获2016年上海市自然科学奖一等奖（第三完成人），2017年国家自然科学奖二等奖（第三完成人）。2017年入选中国科学院青年创新促进会会员，2018年入选上海市青年科技启明星计划（A类），2019年入选中国青年科技工作者协会第六届会员。