Chiral Pyridines for Catalytic Organic Transformation

化学合成项目将资助迈阿密大学的Norito Takenaka教授开发碳-碳键形成反应的不对称有机催化方法，包括氯胺酮烯丙基化和丁基化、准选择性硝基烯Diels-Alder反应和Claisen重排。这些不对称反应将由手性路易斯碱催化剂或Brønsted酸催化剂促进，这些催化剂基于以前未开发的1-扎链烯。研究强调了解螺旋烯衍生的催化剂结构，反应性和选择性也将进行，以加强机理的了解。更广泛的影响包括对本科生和研究生进行现代不对称综合的严格培训，以及通过吸纳历史上在科学领域代表性不足的群体的研究人员来扩大迈阿密大学的参与。更广泛的科学影响包括开发出一种全新的手性催化剂，与化学计量手性试剂相比，它在效率、经济和环境友好方面具有优势。这些进展有望使基础合成研究界以及依赖于获取富含对映体的小有机分子的方法的制药和农业工业受益。这些稳定的催化剂易于操作，这增加了它们对工业和学术科学的影响。

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.