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.
Chemistry Seminar - Dr. Rodney Smith
Posted on 2018-06-18
Dr. Rodney Smith of the University of Waterloo will present a seminar.
Chemistry Seminar - Dr. GianLuigi Botton
Posted on 2018-06-18
Dr. GianLuigi Botton of McMaster University will present a seminar.
Chemistry Special Seminar - Dr. Travis Dudding
Posted on 2018-05-25
Dr. Travis Dudding of Brock University will present a special seminar.
Chemistry Seminar - Theerawat Prasertanan
Posted on 2018-05-10
Theerawat Prasertanan, PhD candidate, will present a seminar.
Chemistry Special Seminar
Posted on 2018-03-29
Prof. Dr. Ingo Krossing of the University of Freiburg, Germany will present a special seminar.
Chemistry Special Seminar - Dr. Raymond J. Andersen
Posted on 2018-03-14
Dr. Raymond J. Andersen, University of British Columbia, will present a special seminar.