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In the Laboratory
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Green Chemistry
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Asymmetric Aldol Reaction Induced by Chiral Auxiliary
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Jorge Pereira
Escola Superior de Tecnologia de Setúbal, Campus do Instituto Politécnico de Setúbal, Estefanilha, 2910-761 Setúbal, Portugal
Carlos A. M. Afonso
CQFM, Departmento de Engenharia Química, Instituto Superior Técnico, 1049-001 Lisboa, Portugal
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September 2006
Vol. 83 No. 9
p. 1333
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| Abstract |
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An asymmetric aldol reaction based on the use of (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one as a chiral auxiliary is described involving a three-step procedure: preparation of the chiral auxiliary from readily available (–)-ephedrine and urea in a solventless fashion, coupling of the chiral auxiliary to the ester functional group, and aldol condensation via in situ formation of the corresponding boron enolate.
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| Supplement |
Detailed procedures of each step, notes for the instructor, sample spectra, and sample HPLC chromatograms are available.
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| More Information |
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Citation |
Pereira, Jorge; Afonso, Carlos A. M. J. Chem. Educ. 2006 83 1333.
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Keywords |
Aldehydes / Ketones; Asymmetric Synthesis; Chirality / Optical Activity; Chromatography; Diastereomers; Hands-On Learning / Manipulatives; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Stereochemistry; Synthesis; Upper-Division Undergraduate
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History |
Created:
Last Updated: |
8/7/2006
8/18/2006
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 Caution! | | Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations. |
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