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Epoxidation of Geraniol: An Advanced Organic Experiment that Illustrates Asymmetric Synthesis
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Abstract
The Sharpless epoxidation reaction is considered one of the most powerful advances in asymmetric organic synthesis (1). It is a classic example of the use of an asymmetric catalyst to provide an enantiomerically enriched mixture of epoxy alcohols. The procedure typically uses titanium(IV) tetraisopropoxide (Ti(OiPr)4) as a catalyst, a peroxide, and dialkyl tartrates to induce asymmetry in the epoxidation reaction of allylic alcohols. The experiment described in this paper illustrates the principle of asymmetric epoxidation and enables students to determine enantiomeric product ratios using chiral shift reagents and NMR spectroscopy.
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
ChromatographyCiting Articles
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This article has been cited by 11 ACS Journal articles (5 most recent appear below).
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Thomas R. Hoye and Christopher S. JeffreyJournal of Chemical Education2006 83 (6), 919The title exercise is presented as a vehicle for gaining proficiency with a type of experiment that novice researchers often consider to be nearly impossible—the isolation and characterization of products from a chemical reaction performed on what would ...
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- Received: August 03, 2009
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