Self-disproportionation of enantiomers of heterocyclic compounds having a tertiary trifluoromethyl alcohol center on chromatography with a non-chiral system

Ogawa, Shin-ichi; Nishimine, Takayuki; Tokunaga, Etsuko; Nakamura, Shuichi; Shibata, Norio

doi:10.1016/j.jfluchem.2009.12.002

Cited by 38 publications

(17 citation statements)

References 79 publications

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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%

Self‐disproportionation of Enantiomers (SDE) of Chiral Nonracemic Amides via Achiral Chromatography

Wzorek

Sato

Drabowicz

et al. 2016

Israel Journal of Chemistry

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This article is based on a review of literature devoted to the phenomenon of SDE via achiral chromatography since the appearance of the seminal work of Professor Emanuel Gil‐Av. The discussed examples of chromatographic studies are related to amides derived from chiral amines and α‐ and β‐amino acids. We discuss the observed SDE magnitude as a function of a compound's structure, and composition of eluent and stationary phases, providing some mechanistic considerations. Particular emphasis is given to the aspect of SDE via achiral chromatography as an emerging unconventional enantiomeric purification technique.

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Section: Discussionmentioning

confidence: 99%

Self‐disproportionation of Enantiomers (SDE) of Chiral Nonracemic Amides via Achiral Chromatography

Wzorek

Sato

Drabowicz

et al. 2016

Israel Journal of Chemistry

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“…(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%

Enantioseparations in Achiral Environments and Chromatographic Systems

Martens

Bhushan

2016

Israel Journal of Chemistry

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Since the very first resolution of racemic tartaric acid by Pasteur, the importance of resolution and methodology has been on a path of continuous understanding and expansion. The science and chemistry of achieving such targets has changed a lot. The advent of chromatography changed the direction by involving synthetic, semisynthetic, or naturally occurring chiral materials for a direct approach to resolution, where rapid and reversible association occurs to form diastereomers with different stabilities and partition coefficients responsible for overall enantioseparation. It has now reached a stage where the separation of excess enantiomers from nonracemic mixtures has been achieved in a totally achiral environment, which does not appear to be in line with the prevalent concepts of basic stereochemistry. Caution should be exercised when enantiomerically enriched mixtures – obtained by enantioselective synthesis – are chromatographed for purification in preparative organic synthesis.

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“…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%

Organocatalytic Enantioselective Nucleophilic Alkynylation of Allyl Fluorides Affording Chiral Skipped Ene‐ynes

et al. 2016

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Asymmetric methods for preparation of chiral alkynyl-containing compounds are in extremely high demand in many sectors of chemical research. In this work, we report the discovery of ag eneral organocatalytic enantioselective alkynylation based on the idea of Si/F activation of the allylic C À Fbond. This approach features reasonably broad substrate scope,functional group tolerance,and relatively neutral, mild, and operationally convenient reaction conditions;all of which bode well for the synthetic value of the discovered method. In particular,this method provides unique chiral skipped 1,4-eneynes having two kinds of versatile functional groups.

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Self-disproportionation of enantiomers of heterocyclic compounds having a tertiary trifluoromethyl alcohol center on chromatography with a non-chiral system

Cited by 38 publications

References 79 publications

Self‐disproportionation of Enantiomers (SDE) of Chiral Nonracemic Amides via Achiral Chromatography

Self‐disproportionation of Enantiomers (SDE) of Chiral Nonracemic Amides via Achiral Chromatography

Enantioseparations in Achiral Environments and Chromatographic Systems

Organocatalytic Enantioselective Nucleophilic Alkynylation of Allyl Fluorides Affording Chiral Skipped Ene‐ynes

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