Stereoselective Reactions of Aromatic Building Blocks

在化学系化学合成项目的支持下，查佩尔山的北卡罗来纳州大学的杰弗里约翰逊教授将研究丰富的芳香族起始材料的反应化学。分子的复杂性和可持续性是化学领域面临的巨大挑战。约翰逊教授和他的团队正在寻求开发新的化学反应，从更简单和丰富的原料化学品产生高度功能化和有用的产品。一些高度功能化的产物有望作为生物活性化合物在化学生物学和药物化学中得到应用。催化将在这些研究中发挥核心作用，有望为化学界提供新的实验工具。研究小组将努力向小学和公众推广，并通过支持科学，技术，工程和数学（STEM）中代表性不足的群体的学生来补充研究影响。高度官能化和立体化学定义的小分子构建块的产生是许多科学工作的核心，特别是在化学生物学应用的化学合成领域。芳香族化合物由于其固有的稳定性和相对的惰性，很少被看作是立体选择性合成非芳香族材料的有用起始分子。约翰逊教授的团队正在寻求一种多管齐下的方法来开发催化途径，将非手性芳族起始材料转化为有用的、立体富集的手性构建单元，包括高度官能化的系统和杂环。约翰逊实验室的目标是在温和条件下通过类卡宾转移和还原等催化脱芳构化反应将非手性芳香化合物转化为手性碳环。该奖项反映了NSF的法定使命，并通过使用基金会的知识价值和更广泛的影响审查标准进行评估，被认为值得支持。

With the support of the Chemical Synthesis program in the Division of Chemistry, Professor Jeffrey Johnson of the University of North Carolina at Chapel Hill will study the reaction chemistry of abundant aromatic starting materials. Molecular complexity and sustainability are considerable challenges for the field of chemistry. Professor Johnson and his team are seeking to develop new chemical reactions that generate highly functionalized and useful products from simpler and abundant feedstock chemicals. It is expected that some of the highly functionalized products will find applications as bioactive compounds in chemical biology and medicinal chemistry. Catalysis will play a central role in these studies, which are expected to provide new experimental tools for the chemical community. The research impacts will be complemented by the research team’s efforts in outreach to elementary schools and the general public, and through support for students from underrepresented groups in science, technology, engineering and mathematics (STEM).The generation of highly functionalized and stereochemically defined small molecule building blocks is central to many scientific endeavors, particularly in the realm of chemical synthesis for applications in chemical biology. Aromatic compounds are seldom viewed as useful starting molecules for stereoselective synthesis of nonaromatic materials due to their inherent stability and relative inertness. Professor Johnson’s team is pursuing a multipronged approach to the development of catalytic pathways that convert achiral aromatic starting materials into useful, stereoenriched, chiral building blocks, including highly functionalized systems and heterocycles. The Johnson laboratory aims to transform achiral aromatic compounds into chiral carbocycles through catalyzed dearomatization reactions such as carbenoid transfer and reduction under mild conditions. Application to the rapid generation of natural products and natural product mimics is expected during the course of these studies.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.