Chiral Pyridines for Catalytic Organic Transformation

通过这一奖项，化学合成计划资助迈阿密大学的Norito Takenaka教授开发用于碳-碳键形成反应的不对称有机催化方法，包括酮胺烯丙化和巴豆基化、选择性硝基-烯烃Diels-Alder反应和Claisen重排。这些不对称反应将由手性Lewis碱催化剂或Brnsted酸催化剂促进，这些催化剂基于以前未被探索的1-氮杂螺烯。此外，还将开展重点研究，重点了解螺烯衍生催化剂的结构、反应活性和选择性，以加强对机理的理解。广泛的影响包括对本科生和研究生进行现代不对称合成方面的严格培训，以及通过纳入迈阿密大学的研究人员来扩大参与，这些研究人员来自历史上在科学界代表性不足的群体。科学上更广泛的影响包括开发一类全新的手性催化剂，与化学计量比的手性试剂相比，它们在效率、经济和环境友好性方面具有优势。这些进展预计将使基础合成研究界以及制药和农业行业受益，这些行业依赖于获得富含对映体的小有机分子的方法。这些板凳稳定催化剂的易操作性增加了它们对工业和学术科学的可能影响。

With this award, the Chemical Synthesis Program is funding Professor Norito Takenaka of the University of Miami to develop asymmetric organocatalytic methods for carbon-carbon bond forming reactions including ketimine allylation and crotylation, periselective nitroalkene Diels-Alder reactions, and Claisen rearrangements. These asymmetric reactions will be promoted by chiral Lewis base catalysts or Brønsted acid catalysts, which are based on previously unexplored 1-azahelicenes. Studies emphasizing understanding helicene-derived catalyst structures, reactivity and selectivity will also be undertaken to enhance mechanistic understanding.Broader impacts include the rigorous training of undergraduate and graduate students in modern asymmetric synthesis, and broadening participation through the inclusion of researchers at the University of Miami from groups that have historically been underrepresented in sciences. The scientific broader impacts include the development of a fundamentally new class of chiral catalysts with advantages in efficiency, economy, and environmental friendliness over stoichiometric chiral reagents. Such advances are expected to benefit the basic synthetic research community, as well as the pharmaceutical and agricultural industries that rely upon methods to access enantio-enriched small organic molecules. The ease of handling these bench-stable catalysts adds to their likely impact upon industrial and academic science.