A discovery-based undergraduate organic chemistry lab experiment has been developed in which students establish the diastereoselectivity of hydride reduction of the a-chiral ketone (±)-benzoin isopropyl ether to erythro and threo diastereomeric alcohols by two different reducing agents. Students achieve this goal by working collaboratively and…

The essential oil of "Nepeta cataria" L. (catnip), an herbaceous plant known popularly as a stimulant for the domestic cat, is enriched in two diastereomeric iridoid lactones (nepetalactones) that vary in ratio. Although the diastereomers are chromatographically separable and exhibit different 1D NMR spectra, it is not possible to…

We introduce students to dimethylsulfoxonium methylide (DMSY) epoxidation of aryl and nonconjugated aliphatic aldehydes and ketones without revealing that DMSY cyclopropanates enones by Michael-initiated ring closure (MIRC). Each student performs the reaction of DMSY with one of nine carbonyl compounds, including four enones, and then analyzes the…

The stereochemical investigation is conducted to give students the combined experience of chemical synthesis of amines and N-heterocycles and structural stereochemical analysis using NMR spectroscopy. Students are introduced to the concept of topicity-stereochemical relationships between ligands within a molecule by synthesizing N,O-acetals.