Development of Novel Stereocontrolled Synthetic Methods Using Hydroxy- and Amino-azoalkenes

有了这个奖项，NSF化学部的化学合成计划正在支持休斯顿大学的Don Coltart教授的研究，以开发构建含氮和含氧杂环的新方法。 杂环是在许多化合物如药物中发现的环状或环状分子结构。 在现有药物中发现的绝大多数含氮和含氧杂环具有扁平或盘状结构。 从这些相对简单的扁平杂环转移到具有更大三维度的杂环，可能有利于改善旨在开发新药的努力。 作为解决这一问题的一种手段，Coltart研究小组正在开发各种合成工具和策略，以使这种三维含氮和含氧杂环能够有效和简单地制备。 该项目的教育方面是针对研究生和本科生在动手实验室研究的培训。 教授科尔塔特还提高了早期职业本科科学学生的认识，在化学科学的非传统职业途径。 Coltart教授和他的学生开发了使用3-氨基-1-偶氮丙烯和3-羟基-1-偶氮丙烯（分别为AAP和HAP）合成饱和和部分饱和（SPS）N-和O-杂环的新方法。 这些化合物可应用于合成生物学上重要的天然产物、药物和其他化合物。 Coltart研究小组确定AAP和HAP表现出1，3-偶极反应性，并且可以与偶极偶联以分别提供SPS N-和O-杂环。 许多配偶体偶极子可用于接合AAP和HAP，并且被用于以立体控制的方式产生广泛的此类杂环化合物，包括γ-内酯、γ-内酰胺、四氢呋喃和吡咯烷。 这项工作的更广泛影响包括招收代表性不足群体的学生学习化学科学，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进行评估，被认为值得支持审查标准。

With this Award, the Chemical Synthesis Program of the NSF Division of Chemistry is supporting the research of Professor Don Coltart of the University of Houston to develop novel ways of constructing nitrogen- and oxygen-containing heterocycles. Heterocycles are cyclic or ring-shaped molecular structures found in many compounds, such as pharmaceutical drugs. The vast majority of nitrogen and oxygen-containing heterocycles that are found in existing pharmaceuticals have a flat or disk-like structure. Moving away from these relatively simple flat heterocycles to ones that have greater three dimensionality may be beneficial in improving efforts aimed at developing new medicines. As a means of addressing this, the Coltart research group is developing a variety of synthetic tools and strategies to enable such three-dimensional nitrogen- and oxygen-containing heterocycles to be made effectively and simply. The educational aspects of this project are directed at the training of both graduate and undergraduate students in hands-on laboratory research. Professor Coltart also increases the awareness of early career undergraduate science students with regard to nontraditional career pathways in the chemical sciences. Professor Coltart and his students develop novel approaches to the synthesis of saturated and partially saturated (SPS) N- and O-heterocycles using 3-amino-1-azopropenes and 3-hydroxy-1-azopropenes (AAPs and HAPs, respectively). These are compounds can be applied to the synthesis of biologically important natural products, drugs, and other compounds. The Coltart research group established that AAPs and HAPs exhibit 1,3-dipolar reactivity and can be coupled with partner dipoles to provide SPS N- and O-heterocycles, respectively. Numerous partner dipoles are available to engage AAPs and HAPs and are being used to generate a wide range of such heterocyclic compounds in a stereocontrolled way, including gamma-lactones, gamma-lactams, tetrahydrofurans, and pyrrolidines. Broader impacts of this work include the recruitment of students from under-represented groups to the chemical sciences, as well as an outreach program to educate undergraduate science students about the very broad range of nontraditional career opportunities available to them with a chemistry education.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.