The application of quasi-enantiomeric trianglamine macrocycles as chiral probes for anion recognition in ion trap ESI mass spectrometry

This paper reports the synthesis and application of quasi-enantiomeric trianglamine macrocycles for chiral analysis using ion trap ESI mass spectrometry. The quasi-enantiomeric macrocycles were shown to display chiroselection towards a series of enantiomerically pure carboxylic acids and therefore act as chiral probes for anions in the gas phase and in solution.

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(2S,3S,12S,13S,22S,23S)-1,4,11,14,21,24-Hexa-aza-(2,3:12,13:22,23)-tributano-(6,9:16,19:26,29)-trietheno-(1H,2H,3H,4H,5H,10H,11H,12H,13H,14H,15H,20H,21H,22H,23H,24H,25H,30H)-octadecahydro-(30)-annuleneC42H54N6Ee >98%[α]D25=+82 (c 0.5, CH2Cl2), CD spectra obtainedSource of chirality: chemical resolution via tartrate saltAbsolute configuration: (all-S)

(2S,3S,12S,13S,22S,23S)-1,4,11,14,21,24-Hexa-aza-(2,3:12,13:22,23)-tributano-(6,9:16,19:26,29)-trietheno-(1H,2H,3H,4H,5H,10H,11H,12H,13H,14H,15H,20H,21H,22H,23H,24H,25H,30H)-octadecahydro-(30)-annuleneC42H60N6Ee >98%[α]D25=+82.0 (c 0.5, CH2Cl2), CD spectra obtainedSource of chirality: chemical resolution via tartrate saltAbsolute configuration: (all-S)

(2R,3R,12R,13R,22R,23R)-1,4,11,14,21,24-Hexa-aza-(2,3:12,13:22,23)-tributano-(7,8′,17,18′,27,28′)-trietheno-(1H,2H,3H,4H,11H,12H,13H,14H,21H,22H,23H,24H)-duodecahydro-(5D,10D,15D,20D,25D,30D)-hexadeutero-(30)-annuleneC42H54D6N6Ee >98%[α]D25=-79.0 (c 0.5, CHCl3), CD spectra obtainedSource of chirality: chemical resolution via tartrate saltAbsolute configuration: (all-R)

(2S,3S,12S,13S,22S,23S)-1,4,11,14,21,24-Hexa-aza-(2,3:12,13:22,23)-tributano-(7,8′,17,18′,27,28′)-trietheno-(1H,2H,3H,4H,11H,12H,13H,14H,21H,22H,23H,24H)-duodecahydro-(5D,10D,15D,20D,25D,30D)-hexadeutero-(30)-annuleneC42H54D6N6Ee >98%[α]D25=+80.1 (c 0.5, CH2Cl2), CD spectra obtainedSource of chirality: chemical resolution via tartrate saltAbsolute configuration: (all-S)