The residual enantiomers of three tris-(3-indolyl)-phosphane oxides bearing different alkyl groups (methyl, ethyl or i-propyl) in position 2 of the indole rings constituting the blades were separated on the immobilized type Chiralpak IC column in polar organic and reversed-phase modes. The good enantioselectivity and versatility of the IC CSP allowed easy isolation of the enantiomerically highly enriched samples suitable for configurational stability studies. The enantiomerization barriers of residual phosphane oxides were evaluated both by off-column techniques (CD signal and enantiomeric purity decay kinetics) and by dynamic enantioselective high-performance liquid chromatography (HPLC).

Determination of the enantiomerization barrier of the residual enantiomers of C3-symmetric Tris[3-(1-Methyl-2-Alkyl)Indolyl]phosphane oxides: case study of a multitasking HPLC investigation based on an immobilized polysaccharide stationary phase / Rizzo, Simona; Menta, Sergio; Benincori, Tiziana; Ferretti, Rosella; Pierini, Marco; Cirilli, Roberto; Sannicolò, Francesco. - In: CHIRALITY. - ISSN 0899-0042. - STAMPA. - 27:12(2015), pp. 888-899. [10.1002/chir.22525]

Determination of the enantiomerization barrier of the residual enantiomers of C3-symmetric Tris[3-(1-Methyl-2-Alkyl)Indolyl]phosphane oxides: case study of a multitasking HPLC investigation based on an immobilized polysaccharide stationary phase

MENTA, SERGIO;PIERINI, MARCO
;
2015

Abstract

The residual enantiomers of three tris-(3-indolyl)-phosphane oxides bearing different alkyl groups (methyl, ethyl or i-propyl) in position 2 of the indole rings constituting the blades were separated on the immobilized type Chiralpak IC column in polar organic and reversed-phase modes. The good enantioselectivity and versatility of the IC CSP allowed easy isolation of the enantiomerically highly enriched samples suitable for configurational stability studies. The enantiomerization barriers of residual phosphane oxides were evaluated both by off-column techniques (CD signal and enantiomeric purity decay kinetics) and by dynamic enantioselective high-performance liquid chromatography (HPLC).
2015
chiral phosphane oxides; chiralpak IC; circular dichroism; dynamic enantioselective HPLC; enantiomerization barrier; enantioselective HPLC; propellers, residual enantiomers; organic chemistry; analytical chemistry; drug discovery3003 pharmaceutical science; pharmacology; catalysis; spectroscopy
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Determination of the enantiomerization barrier of the residual enantiomers of C3-symmetric Tris[3-(1-Methyl-2-Alkyl)Indolyl]phosphane oxides: case study of a multitasking HPLC investigation based on an immobilized polysaccharide stationary phase / Rizzo, Simona; Menta, Sergio; Benincori, Tiziana; Ferretti, Rosella; Pierini, Marco; Cirilli, Roberto; Sannicolò, Francesco. - In: CHIRALITY. - ISSN 0899-0042. - STAMPA. - 27:12(2015), pp. 888-899. [10.1002/chir.22525]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/833947
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