Enantioselective Michael Addition: An Experimental Introduction to Asymmetric Synthesis

Autor/in	Tiano, Martin
Titel	Enantioselective Michael Addition: An Experimental Introduction to Asymmetric Synthesis
Quelle	In: Journal of Chemical Education, 97 (2020) 8, S.2291-2295 (5 Seiten)Infoseite zur Zeitschrift PDF als Volltext Verfügbarkeit
Zusatzinformation	ORCID (Tiano, Martin)
Sprache	englisch
Dokumenttyp	gedruckt; online; Zeitschriftenaufsatz
ISSN	0021-9584
Schlagwörter	Undergraduate Students; Chemistry; Science Experiments; Laboratory Experiments; Spectroscopy + Suchen Sie Ihr Suchwort? Chemie; Laboratory work; Laborarbeit; Spektroskopie
Abstract	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. (As Provided).
Anmerkungen	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
Erfasst von	ERIC (Education Resources Information Center), Washington, DC
Update	2024/1/01