ERIC Number: EJ814857
Record Type: Journal
Publication Date: 2008-Nov
Pages: 4
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
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.)
Descriptors: Organic Chemistry, Student Centered Curriculum, Science Instruction, Majors (Students), College Science, Science Experiments, Science Laboratories
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Publication Type: Journal Articles; Reports - Evaluative
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A