A Click Chemistry Approach to Nitrogen Heterocycles
André K. Issacs, PhD
Associate Professor of Chemistry, College of the Holy Cross
Monday, December 11, 2023
Gateway 1002
12:00pm – 12:50pm
Abstract: My research interest is centered on a very reliable organic reaction - the copper-catalyzed cycloaddition of sulfonyl azides and terminal alkynes (CuAAC). Differential fragmentation of the resulting 1,2,3-triazole generates ketenimines or rhodium carbenoids which readily engage with a variety of nucleophiles to provide access to heterocycles of interest to the synthetic community. We’ve demonstrated the utility of click chemistry in the synthesis of N-Heterocycles such as indolizines, dihydroisoquinolines and as an approach to beta-lactams.
Biography: A native of Jamaica, André moved to the US to attend the College of the Holy Cross where he received his B.A. in Chemistry in 2005. As an undergraduate, he conducted research in the labs of Kevin J. Quinn focusing on the total synthesis of annonaceous acetogenins Muricatacin and Rollicosin. He received his PhD from the University of Pennsylvania in 2011 (under the guidance of Professor Jeffery D. Winkler), where he focused on the design and synthesis of novel steroid-derived inhibitors of Hedgehog-signaling, based on the alkaloid cyclopamine. He worked as a post-doctoral researcher with Professor Richmond Sarpong at the University of California, Berkeley, where he focused on the synthesis of diterpenoids and the radiolabeled insecticide chlorantraniliprole. In 2012, Andre accepted a tenure-track position at the College of the Holy Cross. In 2018, Andre was promoted to the rank of Associate Professor with tenure. In addition to teaching courses in Organic Chemistry, Andre conducts research utilizing copper-mediated organic transformations. He is one of the co-founding members of Outfront - the college's LGBTQ faculty and staff alliance and serves as faculty advisor to several student groups including the Caribbean African Students' Assemblage, acapella group Fools on the Hill and Club Tennis.