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Determination of the Enantiomerization Barrier of the Residual Enantiomers of C 3 ‐Symmetric Tris[3‐(1‐Methyl‐2‐Alkyl)Indolyl]Phosphane Oxides: Case Study of a Multitasking HPLC Investigation Based on an Immobilized Polysaccharide Stationary Phase
Author(s) -
Rizzo Simona,
Menta Sergio,
Benincori Tiziana,
Ferretti Rosella,
Pierini Marco,
Cirilli Roberto,
Sannicolò Francesco
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22525
Subject(s) - chemistry , enantiomer , tris , alkyl , medicinal chemistry , human multitasking , high performance liquid chromatography , chromatography , nuclear chemistry , organic chemistry , biochemistry , psychology , cognitive psychology
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). Chirality 27:888–899, 2015 . © 2015 Wiley Periodicals, Inc.