Diastereoselective hydride transfer enables a synthesis of chiral 1,5-carboxamido-trifluoromethylcarbinols

Roberto Tinelli, Manuel Schupp, Simon Immo Klose, Saad Shaaban, Boris Maryasin, Leticia González, Nuno Maulide (Corresponding author)

Publications: Contribution to journalArticlePeer Reviewed

Abstract

The deployment of fluorinated functional groups has become a widespread tool in medicinal chemistry due to the impact of fluorine on lipophilicity and metabolic stability. Among these compounds, enantiopure secondary trifluoromethylcarbinols are recurrent features in bioactive compounds. Herein, we present a diastereoselective redox-neutral process allowing the stereospecific synthesis of 1,5-carboxamido-trifluoromethylcarbinols through the formal reduction of a trifluoromethylketone into a trifluoromethylcarbinol. A combined experimental and computational investigation unveiled a network of interconnected equilibria leading to a key hydride transfer event.

Original languageEnglish
Pages (from-to)15751-15756
Number of pages6
JournalChemical Science
Volume15
Issue number38
Early online date9 Sep 2024
DOIs
Publication statusPublished - 9 Sep 2024

Austrian Fields of Science 2012

  • 104015 Organic chemistry

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