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A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors Laboratory
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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.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
Aldehydes / KetonesCiting Articles
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
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- Received: August 03, 2009
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