SusChEM: Studies on Catalytic Asymmetric C-H Amination of Alkenes

University Of Louisiana At Lafayette, Lafayette LA

Investigators

Abstract

The Chemical Catalysis Program of the Chemistry Division supports the project by Professor Radhey S. Srivastava and Dr. Siva Murru. Prof. Radhey S. Srivastava is a faculty member in the Department of Chemistry at University of Louisiana at Lafayette. Prof. Srivastava's group is developing novel catalytic systems to convert simple hydrocarbons to value-added products. The main goal of the proposed research is to design and develop novel catalytic systems for the production of valuable molecules that are of industrial significance. The method uses copper catalysts with chiral ligands. The demand for chiral allyl amines has escalated sharply in recent years, driven by the demands in pharmaceuticals, agrochemicals, flavors, fragrances, and materials. In addition, these catalytic methods are potential useful for the total synthesis of bioactive molecules and chiral drugs. The researchers have introduced comprehensive educational and outreach programs associated with intellectual and economic development. Professor Srivastava's group has been working at the interface of organic, organometallics, and catalysis chemistry. This research addresses the development of a direct catalytic asymmetric amination of simple (non-functionalized) allylic carbon-hydrogen (C-H) substrates using hydroxylamines as aminating agents. The prior art on this field used oxidative amination to make chiral N-hydroxy allyl amines that require additional methods to make chiral allyl amines. The main aim is to find suitable catalytic systems that would deliver the chiral allyl amines with high yields and enantioselectivities. This approach includes rational design and synthesis of new chiral ligands and complexes. The research project screens the catalysts under various reaction conditions while varying solvents, temperature, and additives. The next objective is to explore the synthetic applications to access valuable chemicals such as chiral beta-alkyl N-aryl Aza Baylis-Hillman (ABH) adducts, beta-amino esters and beta-lactams, as well as bioactive molecules such as hydroxymethyl docetaxel fragment, Ezetimibe, and Vigabatrin. Another objective is to address mechanistic aspects of the reaction and provide a better understanding of the reaction pathway and the catalytic activity. This objective helps to develop new catalysts and novel synthetic methods. Professor Srivastava's program enhances public awareness of the importance of chemical sciences. Undergraduates, K-12 students, and high school teachers are exposed to cutting-edge science related to chemical catalysis through summer research and teacher training workshops. The education outreach initiatives involve the inclusion of women and underrepresented groups and strengthen competitiveness by promoting enhancement programs such as LSAMP and McNair program to retain students.