Effects of ring substituents on enantioselective recognition of amino alcohols and acids in uryl-based binol receptors

Raju Nandhakumar, Jayoung Ryu, Hyunjung Park, Lijun Tang, Sujung Choi, Kwan Mook Kim

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

The uryl-based binol aldehyde, (S)-2-hydroxy-2′-(3-phenyluryl-benzyl)-1,1′-binaphthyl-3-carboxaldehyde (1), binds 1,2-amino alcohols and amino acids stereoselectively by reversible formation of imine bond. Hydrogen bond (between uryl group and alcohol -OH moiety) plays an important role in the stereoselectivity of amino alcohols. Hence, any substituents on phenyl group in 1 are expected to affect H-bond ability of uryl group. To study the effects of ring substituents on the stereoselective recognition of amino alcohols, (substituted phenyl)uryl-based chiral binol receptors have been prepared. The receptors with electron-donating X substituents have been synthesized from (S)-2-methoxymethoxy-2′-hydroxy-1,1′-binaphthyl-3-carboxaldehyde and X-phenyluryl-benzyl bromide. The receptors with electron-withdrawing Y substituents, however, required a different synthetic strategy including transformation of an aldehyde to alcohol. The incorporation of the electron withdrawing groups slightly accelerated the stereoselective recognition property of the receptor. Though the acceleration is not so remarkable, this work demonstrates the versatile derivatization of 1 in achieving higher stereoselective recognition of 1,2-amino alcohols and stereoconversion of l-amino acids to d-amino acids.

Original languageEnglish
Pages (from-to)7704-7708
Number of pages5
JournalTetrahedron
Volume64
Issue number33
DOIs
StatePublished - 11 Aug 2008

Keywords

  • Electron-withdrawing group effect
  • Stereoconversion
  • Stereoselective recognition

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