Enzymatic Resolution of 1-Phenylethanol and Formation of a Diastereomer: An Undergraduate 1H NMR Experiment To Introduce Chiral Chemistry
This organic laboratory experiment introduces students to stereoselective enzyme reactions, resolution of enantiomers, and NMR analysis of diastereomers. The reaction between racemic 1-phenylethanol and vinyl acetate in hexane to form an ester is catalyzed by acylase I. The unreacted alcohol is then treated with a chiral acid and the resulting ester diastereomer is analyzed by NMR. This experiment is suitable for group work in the laboratory as several diastereomers are synthesized and compared to determine which enantiomer of 1-phenylethanol reacts with the enzyme.
Faraldos, Juan; Giner, José-Luis; Smith, David; Wilson, Mark; Ronhovde, Kyla; Wilson, Erin; Clevette, David; Holmes, Andrea; and Rouhier, Kerry, "Enzymatic Resolution of 1-Phenylethanol and Formation of a Diastereomer: An Undergraduate 1H NMR Experiment To Introduce Chiral Chemistry" (2011). Journal of Chemical Education 88(3): 334-336. Faculty Publications. Paper 58.
Journal of Chemical Education