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Synthesis of chiral vicinal diols and analysis of them by capillary zone electrophoresis
Author(s) -
Liu Peng,
He Wei,
Zhao Yan,
Wang PingAn,
Sun XiaoLi,
Li XiaoYe,
Zhang ShengYong
Publication year - 2008
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.20500
Subject(s) - chemistry , vicinal , capillary electrophoresis , reagent , dihydroxylation , enantiomer , yield (engineering) , chirality (physics) , chiral ligand , enantioselective synthesis , catalysis , combinatorial chemistry , chromatography , stereochemistry , organic chemistry , materials science , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark , metallurgy
This paper describes an improved access to 1,4‐bis (9‐ O ‐quininyl) phthalazine [(QN) 2 PHAL], a very useful chiral ligand for catalytic asymmetric dihydroxylation (AD), by using CaH 2 as acid‐binding reagent in a high yield under mild conditions. The application of (QN) 2 PHAL to the AD reactions of eight olefins exhibited excellent enantioselectivity and activity with corresponding chiral vicinal diols. Furthermore, a capillary zone electrophoresis method was developed to separate the aforementioned chiral vicinal diols by using of neutral β‐cyclodextrin (β‐CD) as chiral selector and borate as running buffer. High resolution was achieved under the optimal conditions of β‐CD 2.2% (w/v), pH 10, 200 mM borate buffer at 15 kV, and 20°C within 15 min. The relative standard deviations of the corrected peak areas and migration time were less than 3.9% and 1.3%, respectively. In addition, the developed method was successfully applied to the determination of the purity and the enantiomeric excesses value (%ee) of the AD reaction products. Chirality, 2008. © 2007 Wiley‐Liss, Inc.