New Chemistry of Nitrodienes

University Of California-Los Angeles, Los Angeles CA

Investigators

Abstract

With this project, the Chemical Synthesis program is supporting Professor Ohyun Kwon of the Department of Chemistry and Biochemistry at the University of California, Los Angeles to systematically study the 6 pi-electrocyclizations of nitrodienes. The 6 pi-electrocyclization of nitrodienes is a new reaction that permits the highly efficient assembly of complex nitroso acetals with predictable stereochemistry and the subsequent capture of the intermediate nitronates through [3+2] dipolar cycloaddition. A key component of these studies relates to the control of olefin geometry in electrocyclizaton precursor. The new tandem electrocyclic ring closure/dipolar cycloaddition will be applied to the construction of heteroatomic nitrogen-containing scaffolds of increasing complexity, including natural product targets. The project will provide a practical and intellectual training environment in modern synthetic organic chemistry methodology development for undergraduate and graduate students and postdoctoral researchers. This skill set can then be applied to tackling problems relevant to industrial, medicinal and agrochemistry, in producing tomorrow's scientists.