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ERIC Number: EJ1442002
Record Type: Journal
Publication Date: 2023-Feb
Pages: 6
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: EISSN-1938-1328
Stereoselective Reduction of [alpha]-Fluoro-[beta]-Ketoesters: Ketoreductases and Dynamic Reductive Kinetic Resolution
Thomas K. Green; Matthew Vanagel; Anil Damarancha; Brandon Showalter; Scott J. Novick; Harvinder Chagger Maniar
Journal of Chemical Education, v100 n2 p745-750 2023
Stereoselective reduction of ketones to alcohols using baker's yeast is a classic experiment in the undergraduate laboratory. Here we illustrate the reduction of racemic ethyl 2-fluoro-3-oxobutanoate to the corresponding alcohol using a set of four commercially available ketoreductases (KREDs). The reaction sets two stereocenters with four stereoisomers possible, with different KREDs selecting for different stereoisomers. Products are characterized by [superscript 1]H and [superscript 19]F NMR spectroscopy to establish diastereomeric and enantiomeric excess. Students learn about dynamic reductive kinetic resolution (DYRKR) and perform NMR Mosher ester analysis for stereochemical assignments.
Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A