Selective synthesis of α,α-dideuterio alcohols by the reduction of carboxylic acids using Smi2 and D2O as deuterium source under set conditions

Michal Szostak, Malcolm Spain, David J. Procter

Research output: Contribution to journalArticle

27 Scopus citations

Abstract

The first general method for the chemoselective synthesis of α,α-dideuterio alcohols directly from feedstock carboxylic acids under single electron transfer conditions using SmI2 is reported. This reaction proceeds after the activation of Sm(II) with a Lewis base, results in excellent levels of deuterium incorporation across a wide range of substrates, and represents an attractive alternative to processes mediated by pyrophoric alkali metal deuterides.

Original languageEnglish (US)
Pages (from-to)5052-5055
Number of pages4
JournalOrganic letters
Volume16
Issue number19
DOIs
StatePublished - Oct 3 2014

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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