Cyclopropenone catalyzed substitution of alcohols with mesylate ion

Eric D. Nacsa, Tristan H. Lambert

Research output: Contribution to journalArticlepeer-review

39 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)38-41
Number of pages4
JournalOrganic Letters
Volume15
Issue number1
DOIs
StatePublished - Jan 4 2013

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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