New C <inf>2</inf>-symmetry diols accumulating one stereogenic axis and two stereogenic centers

Julen Mendizabal, Pedro De March, Josep Recasens, Albert Virgili, Ángel Álvarez-Larena, José Elguero, Ibon Alkorta

Research output: Contribution to journalArticleResearchpeer-review

6 Citations (Scopus)

Abstract

Herein we report a protocol for the enantioselective synthesis of the three stereoisomers of 1,1′-(1,1′-binaphthalene-2,2′-diyl)bis(2,2, 2-trifluoroethanol) and their characterization. These compounds, that combine axial and central chirality, might present interesting properties for enantiorecognition. Different reduction processes were applied to racemic and enantiopure 1,1′-(1,1′-binaphthalene-2,2′-diyl)bis(2,2,2- trifluoroethanone) allowing the isolation of the corresponding ketols, 2,2,2-trifluoro-1-[2′-(2,2,2-trifluoro-1-hydroxyethyl)-1, 1′-binaphthalen-2-yl]ethanone, and the named diols. © 2012 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)9645-9651
JournalTetrahedron
Volume68
Issue number47
DOIs
Publication statusPublished - 25 Nov 2012

Keywords

  • Asymmetric hydrogen transfer
  • Axial chirality
  • Binaphthalenic compounds
  • C -Symmetry diols 2
  • Stereoselective synthesis

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