Cyclopropenone catalyzed substitution of alcohols with mesylate ion.

Eric D Nacsa, Tristan H Lambert

Department of Chemistry, Columbia University, New York, New York 10027, USA.

Organic letters 2013 Jan 4

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The cyclopropenone catalyzed nucleophilic substitution of alcohols by methanesulfonate ion with inversion of configuration is described. This work provides an alternative to the Mitsunobu reaction that avoids the use of azodicarboxylates and generation of hydrazine and phosphine oxide byproducts. This transformation is shown to be compatible with a range of functionality. A cyclopropenone scavenge strategy is demonstrated to aid purification.