Synthesis and enantioselective transport studies of optically active lipophilic proton-ionizable crown ethers containing a diarylphosphinic acid unit

The synthesis of new enantiopure lipophilic crown ethers (S,S)-2, (S,S)-3, (R,R)-3, and (R,R)-4 containing a diarylphosphinic acid unit has been accomplished. The transport ability of these ligands has been studied in an aqueous source phase/lipophilic organic bulk liquid membrane/aqueous receiving phase system controlled by the pH of the media. The enantioselective transport of chiral amines has also been investigated.

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(7S,15S)-2,20-Di-tert-butyl-7,15-didecyl-22-ethoxy-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxa-λ5-phosphacyclooctadecin-22-oneC50H85O7PEe > 99%[α]D25 = +34.5 (c 1.04, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (7S,15S)

(7S,15S)-2,20-Di-tert-butyl-7,15-didecyl-22-ethoxy-4,18-dinitro-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxa-λ5-phosphacyclooctadecin-22-oneC50H83N2O11PEe > 99%[α]D25 = −56.0 (c 1.03, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (7S,15S)

(7S,15S)-7,15-Didecyl-22-ethoxy-2,20-dinitro-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxa-λ5-phosphacyclooctadecin-22-oneC42H67N2O11PEe > 99%[α]D25 = +59.0 (c 0.58, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (7S,15S)

(7S,15S)-2,20-Di-tert-butyl-7,15-didecyl-22-hydroxy-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxa-λ5-phosphacyclooctadecin-22-oneC48H81O7PEe > 99%[α]D25 = +48.7 (c 0.94, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (7S,15S)

(7S,15S)-2,20-Di-tert-butyl-7,15-didecyl-22-hydroxy-4,18-dinitro-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxa-λ5-phosphacyclooctadecin-22-oneC48H79N2O11PEe > 99%[α]D25 = +98.9 (c 1.00, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (7S,15S)

(7R,15R)-7,15-Didecyl-22-hydroxy-2,20-dinitro-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxa-λ5-phosphacyclooctadecin-22-oneC40H63N2O11PEe > 99%[α]D25 = −209.0 (c 1.00, CH2Cl2)Source of chirality: (R)-epoxydodecaneAbsolute configuration: (7R,15R)