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The self‐disproportionation of enantiomers (SDE): The effect of scaling down, potential problems versus prospective applications, possible new occurrences, and unrealized opportunities?

https://doi.org/10.1002/elps.201800414

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Outgoing claims: the papers this work cites, builds on, or argues with.

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Assembly of Fluorinated Quaternary Stereogenic Centers through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions

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Possible Case of Halogen Bond‐Driven Self‐Disproportionation of Enantiomers (SDE) via Achiral Chromatography

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Optical Purifications via Self‐Disproportionation of Enantiomers by Achiral Chromatography: Case Study of a Series of α‐CF3‐containing Secondary Alcohols

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Enantiomer‐Differentiation Induced by an Enantiomeric Excess during Chromatography with Achiral Phases

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Determination of the Dimerization Equilibrium Constants of Omeprazole and Pirkle's Alcohol through Optical‐Rotation Measurements

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Purification of Enantiomeric Mixtures in Enantioselective Synthesis: Overlooked Errors and Scientific Basis of Separation in Achiral Environment

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Terminology Related to the Phenomenon ‘Self‐Disproportionation of Enantiomers’ (SDE)

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Enantiomeric Enrichments via the Self‐Disproportionation of Enantiomers (SDE) by Achiral, Gravity‐Driven Column Chromatography: a Case Study Using N‐(1‐Phenylethyl)acetamide for Optimizing the Enantiomerically Pure Yield and Magnitude of the SDE

inferredcites →https://doi.org/10.1002/ijch.201600077openalex-snapshot

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

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Enantioseparations in Achiral Environments and Chromatographic Systems

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Is it possible to affect the enantiomeric composition by a simple distillation process?

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Remarkable magnitude of the self-disproportionation of enantiomers (SDE) via achiral chromatography: application to the practical-scale enantiopurification of β-amino acid esters

inferredcites →https://doi.org/10.1007/s10337-013-2434-6openalex-snapshot

UHPLC: The Greening Face of Liquid Chromatography

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Computer simulation of three scenarios for the separation of non-racemic mixtures by chromatography on achiral stationary phases

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Resolution of non-racemic mixtures in achiral chromatographic systems: A model for, the enantioselective effects observed

inferredcites →https://doi.org/10.1016/0040-4039(95)00454-kopenalex-snapshot

Enantiomeric enrichment by the use of density differences between racemic compounds and optically active enantiomers

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Catalytic asymmetric synthesis of binaphthol derivatives by aerobic oxidative coupling of 3-hydroxy-2-naphthoates with chiral diamine-copper complex

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General model for the achiral chromatography of enantiomers forming dimers: application to binaphthol

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Elaborate treatment of retention in chemoselective chromatography—The retention increment approach and non-linear effects

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Self-disproportionation of enantiomers via achiral gravity-driven column chromatography: A case study of N -acyl-α-phenylethylamines

inferredcites →https://doi.org/10.1016/j.jfluchem.2005.11.004openalex-snapshot

Self-disproportionation of enantiomers of (R)-ethyl 3-(3,5-dinitrobenzamido)-4,4,4-trifluorobutanoate on achiral silica gel stationary phase

inferredcites →https://doi.org/10.1016/j.jfluchem.2009.10.002openalex-snapshot

Self-disproportionation of enantiomers of 3,3,3-trifluorolactic acid amides via sublimation

inferredcites →https://doi.org/10.1016/j.jfluchem.2009.10.018openalex-snapshot

NMR spectral enantioresolution of spirobrassinin and 1-methoxyspirobrassinin enantiomers using (S)-(−)-ethyl lactate and modeling of spirobrassinin self-association for rationalization of its self-induced diastereomeric anisochromism (SIDA) and enantiomer self-disproportionation on achiral-phase…

inferredcites →https://doi.org/10.1016/j.jfluchem.2009.11.010openalex-snapshot

Self-disproportionation of enantiomers of α-trifluoromethyl lactic acid amides via sublimation

inferredcites →https://doi.org/10.1016/j.jfluchem.2009.11.015openalex-snapshot

Chirality-dependent sublimation of -(trifluoromethyl)-lactic acid: Relative vapor pressures of racemic, eutectic, and enantiomerically pure forms, and vibrational spectroscopy of isolated (S,S) and (S,R) dimers

inferredcites →https://doi.org/10.1016/j.jfluchem.2009.11.026openalex-snapshot

Self-disproportionation of enantiomers of isopropyl 3,3,3-(trifluoro)lactate via sublimation: Sublimation rates vs. enantiomeric composition

inferredcites →https://doi.org/10.1016/j.jfluchem.2016.07.016openalex-snapshot

Self-Disproportionation of Enantiomers (SDE) via achiral gravity-driven column chromatography of N -fluoroacyl-1-phenylethylamines

inferredcites →https://doi.org/10.1016/j.tet.2012.03.054openalex-snapshot

Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography

inferredcites →https://doi.org/10.1016/j.tetasy.2010.04.027openalex-snapshot

Nonlinear effects in enantioselective chromatography: prediction of unusual elution profiles of enantiomers in non-racemic mixtures on an achiral stationary phase doped with small amounts of a chiral selector

inferredcites →https://doi.org/10.1016/j.tetasy.2010.04.040openalex-snapshot

Rational application of self-disproportionation of enantiomers via sublimation—a novel methodological dimension for enantiomeric purifications

inferredcites →https://doi.org/10.1016/j.tetasy.2013.06.008openalex-snapshot

Self-disproportionation of enantiomers of prazoles via achiral, gravity-driven silica gel column chromatography

inferredcites →https://doi.org/10.1016/j.tetasy.2016.03.004openalex-snapshot

Chiral additive induced self-disproportionation of enantiomers under MPLC conditions: preparation of enantiomerically pure samples of 1-(aryl)ethylamines from racemates

inferredcites →https://doi.org/10.1016/j.tetasy.2017.08.020openalex-snapshot

A question of policy: should tests for the self-disproportionation of enantiomers (SDE) be mandatory for reports involving scalemates?

inferredcites →https://doi.org/10.1016/j.tetasy.2017.09.005openalex-snapshot

A fast, new method to enhance the enantiomeric purity of non-racemic mixtures: self-disproportionation of enantiomers in the gas antisolvent fractionation of chlorine-substituted mandelic acid derivatives

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Chiral initiator-induces self-disproportionation of enantiomers via achiral chromatography: application to enantiomer separation of racemate

inferredcites →https://doi.org/10.1016/s0021-9673(01)01366-8openalex-snapshot

Separation of binaphthol enantiomers through achiral chromatography

inferredcites →https://doi.org/10.1016/s0021-9673(01)92750-5openalex-snapshot

Self-amplification of optical activity by chromatography on an achiral adsorbent

inferredcites →https://doi.org/10.1021/ja028403hopenalex-snapshot

Homochiral Supramolecular Polymerization of an “S”-Shaped Chiral Monomer: Translation of Optical Purity into Molecular Weight Distribution

inferredcites →https://doi.org/10.1021/ja065603aopenalex-snapshot

Phenomenon of Optical Self-Purification of Chiral Non-Racemic Compounds

inferredcites →https://doi.org/10.1021/ja067905iopenalex-snapshot

Separation of Racemate from Excess Enantiomer of Chiral Nonracemic Compounds via Density Gradient Ultracentrifugation

inferredcites →https://doi.org/10.1021/jo00081a015openalex-snapshot

Enantiomeric enrichment of sulfoxides by preparative flash chromatography on an achiral phase

inferredcites →https://doi.org/10.1021/jo981808topenalex-snapshot

Enantioselective Synthesis of Binaphthol Derivatives by Oxidative Coupling of Naphthol Derivatives Catalyzed by Chiral Diamine·Copper Complexes

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Measurement of the Dimerization Equilibrium Constants of Enantiomers

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Synthesis, enzymic resolution and enantiomeric enhancement of bis(hydroxymethyl)[7]thiaheterohelicenes

inferredcites →https://doi.org/10.1039/b814905dopenalex-snapshot

NMR and molecular modeling of the dimeric self-association of the enantiomers of 1,1′-bi-2-naphthol and 1-phenyl-2,2,2-trifluoroethanol in the solution state and their relevance to enantiomer self-disproportionation on achiral-phase chromatography (ESDAC)

inferredcites →https://doi.org/10.1039/c2cc37491aopenalex-snapshot

Unconventional preparation of racemic crystals of isopropyl 3,3,3-trifluoro-2-hydroxypropanoate and their unusual crystallographic structure: the ultimate preference for homochiral intermolecular interactions

inferredcites →https://doi.org/10.1039/c2cs35006hopenalex-snapshot

Self-disproportionation of enantiomers via achiral chromatography: a warning and an extra dimension in optical purifications

inferredcites →https://doi.org/10.1039/c4ob00831fopenalex-snapshot

The self-disproportionation of the enantiomers (SDE) of methyl n-pentyl sulfoxide via achiral, gravity-driven column chromatography: a case study

inferredcites →https://doi.org/10.1039/c4ra13928copenalex-snapshot

A comprehensive examination of the self-disproportionation of enantiomers (SDE) of chiral amides via achiral, laboratory-routine, gravity-driven column chromatography

inferredcites →https://doi.org/10.1039/c4sc03047hopenalex-snapshot

Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications

inferredcites →https://doi.org/10.1039/c6ra21253kopenalex-snapshot

Synthesis of fluorinated donepezil by palladium-catalyzed decarboxylative allylation of α-fluoro-β-keto ester with tri-substituted heterocyclic alkene and the self-disproportionation of its enantiomers

inferredcites →https://doi.org/10.1039/c7sc05138gopenalex-snapshot

The self-disproportionation of enantiomers (SDE): a menace or an opportunity?

inferredcites →https://doi.org/10.1055/s-0032-1316812openalex-snapshot

Self-Disproportionation of Enantiomers of Chiral, Non-Racemic Fluoroorganic Compounds: Role of Fluorine as Enabling Element

inferredcites →https://doi.org/10.1080/10826079208018806openalex-snapshot

Resolution of Enantiomers with Achiral Phase Chromatography

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Comparison of UHPLC and HPLC in Benzodiazepines Analysis of Postmortem Samples

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Separation of an Enantiomorph and Its Racemate by Distillation: Strong Chiral Recognizing Ability of Trifluorolactates

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Self-Disproportionation of Enantiomers via Sublimation; New and Truly Green Dimension in Optical Purification

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Self-disproportionation of enantiomers (SDE) of chiral sulfur-containing compounds via achiral chromatography

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Suggested New Terms for Describing Chiral States and the State-Dependent Behavior of Chiral Systems

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Incoming claims: where this work appears in other papers’ reference lists and arguments.

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Altering the mobile phase composition to enhance self-disproportionation of enantiomers in achiral chromatography

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Separation of nonracemic mixtures of enantiomers by achiral simulated moving bed chromatography

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Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

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Coupling Achiral and Chiral Chromatography for Efficient Separation of Enantiomeric Mixtures

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Localized Partitioning of Enantiomers in Solid Samples of Sulfoxides: Importance of Sampling Method in Determination of Enantiopurity

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A Call for a Change in Policy Regarding the Necessity for SDE Tests to Validate the Veracity of the Outcome of Enantioselective Syntheses, the Inherent Chiral State of Natural Products, and Other Cases Involving Enantioenriched Samples

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