2015
DOI: 10.1039/c5cc06306j
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5,5′-Diamino-BIPHEP ligands bearing small selector units for non-covalent binding of chiral analytes in solution

Abstract: A dynamic axially chiral BIPHEP-ligand with 3,5-dichlorobenzoyl amide selector units for non-covalent binding of phenylalanine derivatives has been developed. Interaction studies in solution were performed with rhodium(i) complexes under exclusion of the metal being involved in binding. (Rax, S(Phe)) and (Sax, S(Phe)) adducts were observed as significantly separated species in NMR spectroscopy.

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Cited by 29 publications
(34 citation statements)
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“…45 The effects of non-covalent interaction of 3a and 3b with Ac-(S)-Ala-NHMe, Ac-(S)-Phe-NHMe (S)-4, and Ac-(S)-Phe-(S)-Ala-NHMe (S,S)-5 were investigated via NMR spectroscopy, and signal splitting was observed in 1 H, 19 F{ 1 H}, and 31 P{ 1 H} NMR (see Supporting Information). 45 The effects of non-covalent interaction of 3a and 3b with Ac-(S)-Ala-NHMe, Ac-(S)-Phe-NHMe (S)-4, and Ac-(S)-Phe-(S)-Ala-NHMe (S,S)-5 were investigated via NMR spectroscopy, and signal splitting was observed in 1 H, 19 F{ 1 H}, and 31 P{ 1 H} NMR (see Supporting Information).…”
Section: Resultsmentioning
confidence: 99%
“…45 The effects of non-covalent interaction of 3a and 3b with Ac-(S)-Ala-NHMe, Ac-(S)-Phe-NHMe (S)-4, and Ac-(S)-Phe-(S)-Ala-NHMe (S,S)-5 were investigated via NMR spectroscopy, and signal splitting was observed in 1 H, 19 F{ 1 H}, and 31 P{ 1 H} NMR (see Supporting Information). 45 The effects of non-covalent interaction of 3a and 3b with Ac-(S)-Ala-NHMe, Ac-(S)-Phe-NHMe (S)-4, and Ac-(S)-Phe-(S)-Ala-NHMe (S,S)-5 were investigated via NMR spectroscopy, and signal splitting was observed in 1 H, 19 F{ 1 H}, and 31 P{ 1 H} NMR (see Supporting Information).…”
Section: Resultsmentioning
confidence: 99%
“…In line with our ongoing interest in the design of stereodynamic ligands and catalysts, we determined the interconversion barriers of a variety of BIPHEP and 2,2′‐bis(diphenylphosphoryl)‐1,1′‐biphenyl [BIPHEP(O)] compounds (Figure ) by using enantioselective DHPLC analysis. The corresponding 3,3′‐disubstituted derivatives were prepared by a method reported by Brown et al, and these results are summarized in Table .…”
Section: Resultsmentioning
confidence: 99%
“…It features a tropos biphenyl‐based ligand with a low barrier of inversion . The ligand backbone was modified with interaction sites for efficient noncovalent bonding, which were derived from a chiral recognition system developed by Pirkle and Murray .…”
Section: Introductionmentioning
confidence: 99%