Convenient Formation of Diphenylmethyl Esters Using Diphenylmethyl Trichloroacetimidate

Arijit A. Adhikari, Jigisha P. Shah, Kyle T. Howard, Christopher M. Russo, Daniel R. Wallach, Matthew R. Linaburg, John D. Chisholm

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

Diphenylmethyl trichloroacetimidate is a useful reagent for the protection of carboxylic acids as their corresponding diphenylmethyl esters. These esterifications proceed rapidly without the need for an added catalyst or promoter. A variety of carboxylic acid substrates undergo esterification in excellent yields with the trichloroacetimidate reagent, including substrates possessing acid- or base-sensitive functionality. Protection of a carboxylic acid with a highly enolizable α-stereocenter using diphenylmethyl imidate was also accomplished without racemization.

Original languageEnglish (US)
Article numberST-2013-S0967-L
Pages (from-to)283-287
Number of pages5
JournalSynlett
Volume25
Issue number2
DOIs
StatePublished - Jan 1 2014

Keywords

  • C-O bond formation
  • chemoselectivity
  • esterification
  • esters
  • protecting groups

ASJC Scopus subject areas

  • Organic Chemistry

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