02062nam a22002657a 4500 20231116100201.0 231020b ||||| |||| 00| 0 eng d 0021-9584 RIEBPL Library 540.7 Shuzhe Sun et al... Copper(I)-Catalyzed Kinugasa Reactions in an Undergraduate Organic Chemistry Laboratory (Journal Article) USA :American Chemical Society August 2023 2986-2991 P. American Chemical Society, Volume 100, Issue 8 ***______{For Hard Copy, Please visit Library.}________*** Abstract A β-lactam, the core structure unit of clinically important antibiotics such as penicillin and cephalosporin, is one of the most commonly encountered four-membered heterocycles in organic chemistry and is widely used in medicine and biochemistry. The Kinugasa reaction, a copper(I)-catalyzed cycloaddition of a terminal alkyne with a nitrone, is a straightforward and atom economic approach to 2,3-disubstituted β-lactams. This paper describes a comprehensive chemistry experiment involving the Kinugasa reaction in an advanced undergraduate organic chemistry laboratory course. Undergraduate students perform the Kinugasa reaction on the benchtop and isolate and characterize the β-lactam product. An understanding of this named reaction and the connection of organic chemistry with medicinal chemistry are specially emphasized in the class. Several modern chemistry concepts that are missing from traditional organic courses such as β-lactam chemistry, [3 + 2] cycloaddition, atom economy, and the important role of transition metal catalysis in organic reactions are introduced to students in this course. Comprehensive Chemistry Laboratory Kinugasa Reaction β-Lactam Copper(I) Catalysis Organometallics NMR Spectroscopy Chromatography https://doi.org/10.1021/acs.jchemed.2c01007 PER 0 0 0 0 RIEBPL RIEBPL 2023-11-16 0 540.7 2023-11-16 00:00:00 2023-11-16 PER 44876 44875