Synthesis of Enantiomerically Enriched Mono and Bis 2,2′-Bipyridine Alkyl Sulfoxides and Their First Application as Chiral Auxiliaries

Ławecka, Justyna; Bujnicki, Bogdan; Drabowicz, J.; Łuczak, Jerzy; Rykowski, A.

doi:10.1080/10426500902856347

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Comments Related To Problems With the Accurate Determination1

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Cited by 3 publications

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“…This is based on the fact that the reported enantiomeric excess values differ very much for derivatives having very similar structures. Among them there are papers co-authored by one of us [99][100] devoted to the asymmetric oxidation of 2,2'-bipyridine alkyl sulfides 15a-e to non-racemic 2,2'-bipyridine alkyl sulfoxides 16a-e and bis-sulfoxides 17a-e using either (+)- (8,8-dichlorocamphorylsulfonyl) oxaziridine (method A) 101 or the Kagan reagent (method B) 91 (Scheme 9). Scheme 9.…”

Section: Comments Related To Problems With the Accurate Determinationmentioning

confidence: 99%

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

Drabowicz¹,

Koprowski²,

Wzorek³

et al. 2017

Arkivoc

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This review presents a comprehensive, critical treatment of all the literature data related to the phenomenon of the SDE taking place during gravity-driven achiral chromatography of scalemic compounds bearing sulfoxide and thioamide functionalities. The discussion is focused on the SDE magnitude as a function of the structure iof the compound, composition of eluent and stationary phase, including some mechanistic details. An apparent possibility of application of the SDE phenomenon via achiral chromatography as a novel, emerging unconventional enantiomeric purification technique is also discussed.

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