Cyclopropenone catalyzed substitution of alcohols with mesylate ion

Eric D. Nacsa, Tristan H. Lambert

Research output: Contribution to journalArticle

35 Citations (Scopus)

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

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Mesylates
phosphine
hydrazine
hydrazines
purification
phosphines
alcohols
Substitution reactions
Alcohols
Ions
substitutes
inversions
oxides
configurations
Oxides
Purification
Byproducts
ions
cyclopropenone
methanesulfonic acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Nacsa, Eric D. ; Lambert, Tristan H. / Cyclopropenone catalyzed substitution of alcohols with mesylate ion. In: Organic Letters. 2013 ; Vol. 15, No. 1. pp. 38-41.
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Cyclopropenone catalyzed substitution of alcohols with mesylate ion. / Nacsa, Eric D.; Lambert, Tristan H.

In: Organic Letters, Vol. 15, No. 1, 04.01.2013, p. 38-41.

Research output: Contribution to journalArticle

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