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Cyclopropenone Catalyzed Substitution of Alcohols with Mesylate Ion

Eric D. Nacsa and Tristan H. Lambert*

*Department of Chemistry, Columbia University, New York, New York 10027, United States, Email: tl2240columbia.edu

E. D. Nacsa, T. H. Lambert, Org. Lett., 2013, 15, 38-41.

DOI: 10.1021/ol302970c (free Supporting Information)


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Abstract

The cyclopropenone catalyzed nucleophilic substitution of alcohols by methanesulfonate ion with inversion of configuration provides an alternative to the Mitsunobu reaction. The new reaction avoids the use of azodicarboxylates and generation of hydrazine and phosphine oxide byproducts and is compatible with a range of functionality.

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Key Words

Alcohols, Organocatalysis


ID: J54-Y2013-0000