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ERIC Number: EJ838944
Record Type: Journal
Publication Date: 2009-Jan
Pages: 4
Abstractor: As Provided
Reference Count: 26
ISSN: ISSN-0021-9584
Microscale Synthesis of Chiral Alcohols via Asymmetric Catalytic Transfer Hydrogenation
Peeters, Christine M.; Deliever, Rik; De Vos, Dirk
Journal of Chemical Education, v86 n1 p87-90 Jan 2009
Synthesis of pure enantiomers is a key issue in industry, especially in areas connected to life sciences. Catalytic asymmetric synthesis has emerged as a powerful and practical tool. Here we describe an experiment on racemic reduction and asymmetric reduction via a catalytic hydrogen transfer process. Acetophenone and substituted acetophenones are reduced by NaBH[subscript 4] either in the presence or in the absence of beta-cyclodextrin, and by isopropanol in the presence of a rhodium catalyst with cyclopentadienyl and 1-amino-2-indanol ligands. After analysis by chiral gas chromatography, enantiomeric excess, conversion, and turnover frequency can be calculated. This experiment is suitable for upper-level undergraduate students. The experiment can be completed in a four hour laboratory session. It can also be extended in many ways: the influence of parameters such as reaction time; catalyst or substrate concentration; or temperature or catalyst type can be analyzed. (Contains 2 schemes, 1 figure, and 1 table.)
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 - Descriptive
Education Level: Higher Education
Audience: Teachers
Language: English
Sponsor: N/A
Authoring Institution: N/A
Identifiers - Location: Belgium