News & Events
Chemistry Weekly Seminar - Steven Langdon
Posted on 2017-09-20 in Events
Oct 20, 2017
Harnessing organocatalysis for synthesis:
DFT and Experimental Examination of the N-Heterocyclic Carbene-Catalyzed Cross-Benzoin reaction
The benzoin reaction represents a well-known yet underutilized route to products containing α-hydroxy ketones. N-Heterocyclic Carbenes (NHCs) catalyze the coupling of two aldehydes in an umpolung process, forming a new carbon-carbon bond and a new stereocentre in the process. Although exquisite enantioselective approaches to homo-benzoin products are well established, until recently chemoselectivity issues have rendered high yielding aldehyde-aldehyde cross-benzoin reactions largely unfeasible. Several approaches are capable of generating cross-benzoin products in reasonable yields, however these typically rely on substrate control; couplings of aldehydes with ketones, sterically hindering one partner, or using pre-formed Breslow intermediates all furnish cross-benzoin products with high chemoselectivity. Work in our group has shown that chemoselective cross-benzoin couplings of aromatic and aliphatic aldehydes can be obtained using morpholinone- or piperidinone-based triazolium salts. A combination of computational and experimental work has been used to explore the origin of chemoselectivity in these systems. Ongoing work based on these computational models seeks to expand potential applications of the chemoselective cross-benzoin reaction through rational modification of the catalyst.
Special Seminar - Dr. Amy Stevens
Posted on 2019-02-08
Dr. Amy Stevens, Department of Chemistry, will present a seminar
Chemistry Weekly Seminar - PhD Candidate Amara Zuhaib
Posted on 2019-01-25
Amara Zuhaib, PhD Candidate, will present a seminar at 2:30 p.m. in Thorvaldson 271.
Special Seminar - Dr. Joe B. Gilroy
Posted on 2019-01-21
Dr. Joe B. Gilroy will present a Special Seminar at 10:30 in Thorvaldson 205A
Spinks Lecture Series - Dr. Chris Chang
Posted on 2018-12-17
Dr. Chris Chang, University of California, Berkley
Chemistry Weekly Seminar - Dr. Scott Murphy
Posted on 2018-12-17
Dr. Scott Murphy, Department of Chemistry & Biochemistry at The University of Regina, will present a seminar at 4:00 p.m. in Thorvaldson 271.