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Synfacts 2007(6): 0614-0614  
DOI: 10.1055/s-2007-968504
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Lewis Acid-Lewis Base Ring Opening of Epoxides

Contributor(s): Hisashi Yamamoto, Marina Naodovic
S. E. Denmark*, P. A. Barsanti, G. L. Beutner, T. W. Wilson
University Of Illinois, Urbana, USA
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Publication History

Publication Date:
22 May 2007 (online)

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Significance

The authors describe a possible mechanism based on the number of detailed experiments conducted. An interesting finding presented here is the different binding mode of the epoxide comparing to the carbonyls (carbonyl group binds two molecules of phosphoramide while epoxides are limited to only one), probably due to the specific structural feature of the epoxide group.