Microscale laboratory procedure for undergraduate organic chemistry students when learning about chirality and stereochemistry

CHED 379

Casey L. Gustafson, casey.gustafson@doane.edu and Andrea E. Holmes, andrea.holmes@doane.edu. Department of Chemistry, Doane College, 1014 Boswell, Crete, NE 68333
We designed a microscale synthesis of a bisalkylated L-Alanine derivative. The synthesis, characterization, and chiroptical properties of the L-alanine derivative will be reported. We used the exciton chirality method to assign absolute configuration of the derivative. Two quinolines were used to alkylate L-Alanine followed by complexation with Cu(II) to create a conformationally rigid, asymmetric product. This species featured a right-handed helical conformation of the chromophores and a negative couplet in circular dichroism indicating an S-configuration. This procedure teaches students at Doane College classic organic synthesis, purifications, and characterization methods, but most importantly, they learn how the absolute configuration of a chiral amine is related to chiroptical spectroscopy.