3,5-Dinitrobenzoylphenylglycine Analogues Bearing the 1,1′-Binaphthalene Moiety − Synthesis, Conformational Study, and Application as Chiral Solvating Agents

Abstract

The two new diastereoisomeric chiral auxiliaries (aR,R)-2Ј-Hydroxy-1,1Ј-binaphthyl-2-yl [(3,5-dinitrobenzoyl)amino]-(phenyl)acetate and (aR,S)-2Ј-Hydroxy-1,1Ј-binaphthyl-2-yl [(3,5-dinitrobenzoyl)amino](phenyl)acetate have been synthesised and their efficiency as chiral solvating agents for the

Chiral Reagents for the Determination of Enantiomeric Excess and Absolute Configuration Using NMR Spectroscopy

“…A 3,5dinitrobenzoylphenylglycine derivative with the 1,1Јbinaphthalene moiety was an effective CSA for amines and amides. 107 A 3,3Ј-bridged-1,1Ј-binaphthol dimer in which the bridge was a p-phenylene bis(2-ethynyl) spacer forms a host dimer that will discriminate compounds such as ␣-phenylethyl amine and ␣-amino acid esters. 108 The bis-(tetrachlorobenzenediolato)mono([1,1Ј]-binaphthalenyl-2,2Ј-diolato)phosphate anion was shown to be an effective C S A f o r s a l t s s u c h a s N , N Ј , N Љ -t r i m e t h y l -( 1phenylethyl)ammonium iodide, with separations as large as 0.29 ppm observed for some signals of cationic enantiomers.…”