Organic Chemistry Seminar

Wednesday, March 26, 2014

2:00pm to 3:00pm

Noyes 153 (J. Holmes Sturdivant Lecture Hall)

Ring Fragmentations and Cationic Heteroallenes: Unconventional Routes to Nitrogen Heterocycles

Matthias Brewer, Associate Professor of Chemistry, Department of Chemistry, The University of Vermont,

In this presentation I will discuss two ongoing projects that focus on developing new synthetic organic methods for the preparation of nitrogen-containing heterocycles. In the first portion of my talk I will describe our studies of the intramolecular reactivity of 1-aza-2-azoniaallene salts. We have discovered that these somewhat esoteric heteroallene intermediates have a surprisingly diverse reactivity profile that can lead to the formation of several structurally-distinct and useful heterocyclic scaffolds. In the second portion of my talk I will describe the development of a novel ring fragmentation / intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction sequence that constitutes an efficient three-step route to polycyclic 2,5-dihydropyrroles from α-silyloxy ketones. Recent applications of this reaction sequence in alkaloid natural product synthesis will also be described.

For more information, please contact Lynne Martinez by phone at 626-395-4004 or by email at [email protected].

Event Series

Organic Chemistry Seminar Series

Event Sponsors

Division of Chemistry and Chemical Engineering More Events from this Sponsor