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ERIC Number: EJ1269331
Record Type: Journal
Publication Date: 2020-Aug
Pages: 5
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
Available Date: N/A
Enantioselective Michael Addition: An Experimental Introduction to Asymmetric Synthesis
Journal of Chemical Education, v97 n8 p2291-2295 Aug 2020
We adapted a classical asymmetric Michael addition for a 1 day experimental session (6-8 h) for third- or fourth-year undergraduate students. The experiment contains three steps: synthesis of a chiral Lewis acid, LiAl((S)-BINOL)[subscript 2], then its use as a catalyst in the Michael addition of diethyl malonate on cyclopentenone, followed by purification through column chromatography on silica gel. The desired product can be fully characterized by 1D and 2D NMR experiments and IR spectroscopy. The enantiomeric excess can be determined by polarimetry and [superscript 1]H NMR using the chiral lanthanide shift reagent Eu(hfc)[subscript 3]. This laboratory experiment bridges the gap between theoretical courses about asymmetric reactions and practical implementations of enantioselective reactions.
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