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ERIC Number: EJ814857
Record Type: Journal
Publication Date: 2008-Nov
Pages: 4
Abstractor: As Provided
Reference Count: 10
ISSN: ISSN-0021-9584
A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors Laboratory
Lazarski, Kiel E.; Rich, Alan A.; Mascarenhas, Cheryl M.
Journal of Chemical Education, v85 n11 p1531-1534 Nov 2008
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.)
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:; Web site:
Publication Type: Journal Articles; Reports - Evaluative
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A