Green asymmetric synthesis, an upper-level undergraduate, research based laboratory course

CHED 53

Deborah S Bass, deborah.bass@simmons.edu, Jennifer N. Boice, jennifer.boice@simmons.edu, Jessica E. Haffner, haffner@simmons.edu, Henglian Huang, henglian.huang@simmons.edu, Virgina S Liu, virginia.liu@simmons.edu, Brittany M. Oheim, brittany.oheim@simmons.edu, Shun Yi Tsui, shunyitsui@gmail.com, Aisha A. Warsame, aisha.warsame@simmons.edu, Nancy E. Lee, nancy.lee@simmons.edu, and Richard W. Gurney, richard.gurney@simmons.edu. Department of Chemistry, Simmons College, 300 The Fenway, Boston, MA 02115
Herein, an upper-level undergraduate chemistry course in green chemistry and asymmetric synthesis is described. Because green chemistry is a relatively new field, the process of “greening” has not been extensively applied to asymmetric synthesis in the undergraduate lectures or laboratory. Within this research-based laboratory course, we worked toward producing important, highly-prized, single-handed molecules by exploring various green processes. Taking into account the traditional metrics such as cost, percent yield and purity, students investigated greener solvents, catalysts, reaction conditions and alternative heating methods and applied standardization using green metrics developed at Simmons. Using these methods, we collectively produced (-)-L-lactic acid, (-)-ethyl L-lactate, and pyruvic acid from post-consumer waste polylactic acid (PLA) which is used as cold beverage and food containers in our cafeteria. In addition, students are exploring ways to use these chiral compounds to induce asymmetric reduction of ketones.