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Cyclopropenone catalyzed substitution of alcohols with mesylate ion.

Authors
  • Nacsa, Eric D
  • Lambert, Tristan H
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Jan 04, 2013
Volume
15
Issue
1
Pages
38–41
Identifiers
DOI: 10.1021/ol302970c
PMID: 23237617
Source
Medline
License
Unknown

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.

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