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ERIC Number: EJ998976
Record Type: Journal
Publication Date: 2012-Jun
Pages: 3
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
The Petasis Reaction: Microscale Synthesis of a Tertiary Amine Antifungal Analog
Koroluk, Katherine J.; Jackson, Derek A.; Dicks, Andrew P.
Journal of Chemical Education, v89 n6 p796-798 Jun 2012
Students prepare a tertiary amine antifungal analog in an upper-level undergraduate organic laboratory. A microscale Petasis reaction is performed to generate a liquid compound readily characterized via IR and proton NMR spectroscopy. The biological relevance of the product is highlighted, with the tertiary amine scaffold being an important treatment option for resistant bacterial and fungal infections. The procedure allows for postlaboratory discussion of nitrogen as a stereocenter in an ammonium ion, along with principles of combinatorial chemistry and green chemistry. Deliberation of potential mechanisms for the Petasis reaction provides another valuable learning opportunity for students. (Contains 2 figures and 2 schemes.)
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: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A