Resolution of (±)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid using (1R,2R)-trans-cyclohexane-1,2-diamine

A simple and efficient method has been developed to resolve (+/-)-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylic acid [(+/-)-BINOL-3,3'-dicarboxylic acid] (+/-)-1 using inexpensive and readily accessible chiral resolving agent (1R,2R)-trans-cyclohexane-1,2-diamine 2. Enantiomers of BINOL-3,3'-dicarboxylic acid were obtained in good yields and enantiomeric purity, for example, (S)-(-)-1 was isolated in 34% yield with >99% ee and (R)-(+)-1 was obtained in 36% yield with >99% ee. The formation of diastereomeric salt A between (S)-BINOL-3,3'-dicarboxylic acid and (1R,2R)-trans-cyclohexane-1,2-diamine was ascertained by using IR, single crystal X-ray crystallography, and HRMS. (C) 2015 Elsevier Ltd. All rights reserved.