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The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 17 (2012) pp 223-225
DOI 10.1007/s00897122466

Organocatalytic Enantioselective 1,4-Addition as a Capstone Experiment in Organic Chemistry

Kenneth E. Walsh and Edmir O.Wade*

University of Southern Indiana, 8600 University Blvd Evansville IN, 47712,
Received December 15, 2011. Accepted August 10, 2012.

Published: 30 November 2012

Abstract. We have developed a capstone experiment involving the enantioselective 1,4-addition between N,N-dimethyl-m-anisidine to crotonaldehyde in the presence of an imidazolidinone organocatalyst. The exercise exposes students to contemporary areas of research while utilizing reactions commonly seen in the sophomore organic chemistry sequence. We emphasize the significance of enantioselective organic transformations and the relevance of this area of research to the pharmaceutical industry. We present the exercise as an alternative to methods requiring the use of air sensitive and expensive reagents like transition metal catalysts; the availability and ease-of-use of organocatalysts make them ideal for use in the undergraduate laboratory.

Key Words: In the Classroom; organic chemistry

(*) Corresponding author. (E-mail:

Article in PDF format (102 KB) HTML format

Supporting Materials:

The laboratory handout, spectral data and notes for instructors are available in the supporting materials. (156 KB)

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