ERIC Number: EJ1113958
Record Type: Journal
Publication Date: 2016-Sep
Pages: 5
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
Available Date: N/A
Synthesis of an Imidazolidinone Organocatalyst and Its Application in a Diels-Alder Cycloaddition: A Multistep Experiment for the Organic Teaching Laboratory
Murphy, John J.; Driver, Ross B.; Walsh, Ria; Stephens, John C.
Journal of Chemical Education, v93 n9 p1626-1630 Sep 2016
The development of novel, high-yielding, and selective methodologies for the asymmetric synthesis of stereocenters is at the forefront of modern synthetic chemistry research. Organocatalysis can now be viewed as a viable alternative to the use of the sometimes toxic transition-metal catalysts. In this experiment, the simple synthesis of an achiral imidazolidinone organocatalyst is described and its performance is compared to that of a related commercially available chiral catalyst in a Diels-Alder cycloaddition. The organocatalyst operated via an iminium ion intermediate and the product of the Diels-Alder cycloaddition was purified by silica plug filtration (no flash column chromatography required). The diastereoselectivity was readily measured with [superscript 1]H NMR spectroscopy and optionally, the enantioselectivity of the chiral catalyst can be assessed with chiral GC. The experiment can be performed over three laboratory sessions and is suitable for a third- or fourth-year undergraduate laboratory curriculum. The experiment demonstrated not only the synthesis of an organocatalyst but also the effect and importance of catalyst design on the stereochemical outcome of a Diels-Alder cycloaddition.
Descriptors: Science Instruction, College Science, Organic Chemistry, Science Laboratories, Hands on Science, Spectroscopy, Science Experiments, Laboratory Experiments
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
Author Affiliations: N/A