ERIC Number: EJ1113958
Record Type: Journal
Publication Date: 2016-Sep
Abstractor: As Provided
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
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Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Authoring Institution: N/A
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