SusChEM: Direct functionalization of aldehydes enabled by aminocatalysis

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The Chemical Synthesis Program of the NSF Chemistry Division supports the research of Professor Wei Wang in the Department of Chemistry & Chemical Biology at the University of New Mexico. Professor Wang and his students develop cost-effective and environmentally friendly technologies for organic synthesis based on the concept of aminocatalysis. The goal of this research is to develop and exploit new organocatalytic activation modes for organic transformations. New chemistries are transformed into powerful synthetic methods for the facile and atom-economic synthesis of versatile building blocks starting from simple and readily available chemicals. The syntheses are also conducted under mild reaction conditions. These "one-pot" cascade methods, used to make complex molecular architectures, address critical challenges in modern organic synthesis. The methods include the improvement of synthetic efficiency, the use of sustainable and inexpensive chemicals, the avoidance of toxic agents, and the reduction of waste and hazardous byproducts. As a consequence of operational simplicity, mild reaction conditions and environmental friendliness, this research is well suited for the education of scientists at all levels. Professor Wang's group is well positioned to provide education and training for students from groups that are underrepresented in science.This project continues efforts aimed at expanding the scope of aminocatalysis beyond the well-established activation modes of enamine and iminium catalysis. Professor Wang and his team challenge mechanistic dogma by showing that amine moieties in adducts which result from nucleophilic additions to iminum ions can serve as leaving groups in ensuing nucleophilic substitution reactions. In situ release of the intermediate amine addition products creates a new scenario for aminocatalytic direct functionalization of aldehydes. This research demonstrates that through careful manipulation of the electronic and steric properties of catalysts and reactants, judicious design and selection of amine catalysts, and optimization of reaction conditions, new and powerful catalytic cascade reactions are developed. Given the ready accessibility, reactivity and broad structural diversity of aldehydes, a wide array of new synthetic building blocks and biologically-important complex molecular architectures are constructed in efficient one-pot reactions. The educational plan continues a tradition to recruit undergraduate students especially from underrepresented minority groups over the summer to conduct research in Dr. Wang's laboratory. Dr. Wang also integrates the research results and experiments from in his academic laboratory into his undergraduate students' experiences.