Research

Characterizing the chemical reactivity of understudied nitrogen-containing moieties is critical to uncovering novel synthetic routes. The 2H-azirine moiety is often used as a synthetic intermediate to access azole and azine derivatives in addition to complex polyheterocyclic scaffolds. The reactivity of α,β-unsaturated carbonyls is extraordinarily well-characterized, as these moieties are critical building blocks for making atom-economical asymmetric carbon-carbon bonds, and other heteroatom bonds through conjugate addition reactions. Regioselectivity between the two electrophilic sites on the α,β-unsaturated carbonyls can be controlled to favor either the 1,2- or 1,4-addition products by altering solvents, nucleophiles, and substituents. The well-characterized reactivity of α,β-unsaturated carbonyls has been essential to the development of covalent inhibitors. Visually, we could expect the reactivity of  α,β-unsaturated 2H-azirines to parallel that of α,β-unsaturated carbonyls which could poise the 2H-azirine moiety to an be equally valuable covalent inhibitor affording unique chemical space. However, the reactivity of α,β-unsaturated 2H-azirines remains completely unexplored. 

We are working to provide synthetic access to a diverse set of α,β-unsaturated 2H-azirines through a modular synthetic route. This is in an effort to develop a comprehensive reactivity profile of these unique moieties. 

Rare bacterial amino-sugars are types of sugars exclusively biosynthesized by specific bacteria. These sugars are considered "synthetically inaccessible" by chemists due to the challenging nature of certain chemical manipulations on this scaffold. Chemoenzymatic strategies have been the most used in research, which has vastly improved our knowledge of the biological roles of these complex scaffolds. We aim to complement this research by producing these sugars through higher yielding, scalable synthetic organic routes.