Synthesis of Chiral Crown Ethers Derived from trans, trans- and cis, trans-2,2′-Spirobiindan-1,1′-diols. Their Chiral Recognition and Complexation Properties

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Abstract
Trans,trans-2,2′-Spirobiindan-1,1′-diol (1) was resolved as its (−)-ω-camphanic ester and the absolute rotation of the glycol 1 was determined. Two crown ethers and the acyclic analog were derived from (+)-1. Two crown ethers incorporating (+)-cis,trans-2,2′-spirobiindan-1,1′-diol were also prepared. Their chiral recognition properties in transport of methyl (±)-phenylglycinate hydrochloride and abilities to extract alkali metal picrates were investigated.