2010
DOI: 10.1016/j.jfluchem.2009.12.002
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Self-disproportionation of enantiomers of heterocyclic compounds having a tertiary trifluoromethyl alcohol center on chromatography with a non-chiral system

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Cited by 38 publications
(17 citation statements)
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“…The number and variety of the reported examples evidently suggests that a relatively strong SDE magnitude will be observed in virtually any case where a chiral amide is subjected to achiral chromatography. These overwhelming data clearly identify an amide functionality as an SDE‐phoric group, along with chiral sulfoxides and fluorine‐containing compounds ,,. Thus, it would be reasonable to expect that the editorial policy of chemistry journals should include the request to perform a proper SDE test for papers dealing with catalytic chemical or enzymatic asymmetric synthesis of amide, fluorine, and sulfoxide group‐containing compounds .…”
Section: Discussionmentioning
confidence: 99%
“…The number and variety of the reported examples evidently suggests that a relatively strong SDE magnitude will be observed in virtually any case where a chiral amide is subjected to achiral chromatography. These overwhelming data clearly identify an amide functionality as an SDE‐phoric group, along with chiral sulfoxides and fluorine‐containing compounds ,,. Thus, it would be reasonable to expect that the editorial policy of chemistry journals should include the request to perform a proper SDE test for papers dealing with catalytic chemical or enzymatic asymmetric synthesis of amide, fluorine, and sulfoxide group‐containing compounds .…”
Section: Discussionmentioning
confidence: 99%
“…(xii) Purification of a nonracemic sample of 1‐(3,4‐dimethoxyphenethyl)‐3 hydroxy‐3‐(trifluoromethyl)‐6,7‐dihydro‐1 H ‐indole‐2,4(3 H ,5 H )‐dione from 52 % ee to 99.9 % ee using a column packed with achiral flash silica gel;…”
Section: Separation Of Enantiomers In the Absence Of Any External Somentioning
confidence: 99%
“…As should be routinely done in any research on catalytic asymmetric synthesis, [13] we conducted SDE (self-disproportionation of enantiomers) tests using achiral chromatography [14] and sublimation. [15] Among the products (R)-2,w e selected compound (R)-2a as am odel substrate to carry out the SDE tests.Both sublimation and achiral chromatography tests gave negative results,s uggesting that the isolation of compounds (R)-2 by routine column chromatography and their drying in high vacuum are safe and do not alter the original enantiomeric composition.…”
Section: Angewandte Chemiementioning
confidence: 99%