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ERIC Number: EJ1073064
Record Type: Journal
Publication Date: 2015-Aug
Pages: 4
Abstractor: As Provided
ISSN: ISSN-0021-9584
Alkaloid-Derived Thioureas in Asymmetric Organocatalysis: A Cooperative Learning Activity in a Project-Based Laboratory Course
Monge, David
Journal of Chemical Education, v92 n8 p1390-1393 Aug 2015
An experiment carried out by advanced undergraduate students in a project-based laboratory course is described. Taking into account the positive effects of working in teams, which has been key for successful research in industry and academia, a cooperative learning experience in the laboratory was developed. Students working in teams of four synthesize two alkaloid-derived thioureas starting from a chiral pool (quinidine and quinine). The thioureas are used to catalyze an enantioselective Michael reaction between acetylacetone and "trans"-4-methyl-"ß"-nitrostyrene, providing a platform for discussion of stereochemistry and chirality transfer events. Qualitative analysis of the reaction enantioselectivity is performed by polarimetry, which allows students to assign product optical rotations (+/-) with their absolute configurations (S/R). Students are exposed to an entire research process: analysis of primary literature, discussion with colleagues, planning laboratory schedules, and execution of experiments.
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A