A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors Laboratory

Autor/inn/en	Lazarski, Kiel E.; Rich, Alan A.; Mascarenhas, Cheryl M.
Titel	A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors Laboratory
Quelle	In: Journal of Chemical Education, 85 (2008) 11, S. 1531-1534Infoseite zur Zeitschrift PDF als Volltext Verfügbarkeit
Sprache	englisch
Dokumenttyp	gedruckt; online; Zeitschriftenaufsatz
ISSN	0021-9584
Schlagwörter	Forschungsbericht; Organic Chemistry; Student Centered Curriculum; Science Instruction; Majors (Students); College Science; Science Experiments; Science Laboratories + Suchen Sie Ihr Suchwort? Organische Chemie; Teaching of science; Science education; Natural sciences Lessons; Naturwissenschaftlicher Unterricht
Abstract	The Robinson annulation is a topic of importance in the second-year organic curriculum. A one-pot, enantioselective Robinson annulation is described. The experiment is completed in two lab periods and is geared towards the second-year organic chemistry major. To our knowledge, this is the first example of a one-pot enantioselective Robinson annulation in a second-year organic lab setting. Reaction between methyl vinyl ketone and 2-methyl-1,3-cyclohexanedione in the presence of a catalytic amount of ("S")-proline results in the formation of the Wieland-Miescher ketone in 75% yield and an 84:16 enantiomer ratio. The product is purified easily by silica gel chromatography, and enantioselectivity is determined by either chiral HPLC or chiral GC. The catalyst used in the reaction, ("S")-proline, is an organocatalyst and is moisture- and oxygen-tolerant and nontoxic. Thus the experiment is classified by many to fall within the category of green chemistry. (Contains 3 figures.) (As Provided).
Anmerkungen	Division of Chemical Education of the American Chemical Society. Subscription Department, P.O. Box 1267, Bellmawr, NJ 08099-1267. Tel: 800-691-9846; Tel: 856-931-5825; Fax: 856-931-4115; e-mail: jchemed@egpp.com; Web site: http://www.jce.divched.org
Begutachtung	Peer reviewed
Erfasst von	ERIC (Education Resources Information Center), Washington, DC
Update	2017/4/10