Chemistry of oxaziridines. 8. Asymmetric oxidation of nonfunctionalized sulfides to sulfoxides with high enantioselectivity by 2-sulfamyloxaziridines. Influence of the oxaziridine C-aryl group on the asymmetric induction

Davis, Franklin A.; McCauley, John P.; Chattopadhyay, Sankar; Harakal, Mark E.; Towson, James C.; Watson, William H.; Tavanaiepour, Iraj

doi:10.1021/ja00245a030

Cited by 82 publications

(25 citation statements)

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“…The PFBA reacts with aromatic amines in alcohol to afford high yields of Schiff bases (Scheme 43 [16,[482][483][484][485][486][487][488][489][490][491][492][493][494][495][496][497][498][499]). …”

Section: Chemical Reactions Of Pentafluorobenzaldehyde With Nitrogen mentioning

confidence: 99%

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Pažitný

Solčan

Végh

2009

Journal of Fluorine Chemistry

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Section: Chemical Reactions Of Pentafluorobenzaldehyde With Nitrogen mentioning

confidence: 99%

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Pažitný

Solčan

Végh

2009

Journal of Fluorine Chemistry

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“…Sulfamyloxaziridines offer two practical advantages over sulfonyloxaziridines -it is easier to vary their structure and they are chromatographically more stable, and therefore, easier to purify and isolate. 139 Davis investigated camphorylsulfonyloxaziridine 143 but the results obtained were inferior to those obtained using sulfamyloxaziridines. 140 Later investigations by Davis using dichlorocamphorylsulfonyloxaziridine 144 were much more successful.…”

Section: Scheme 58mentioning

confidence: 97%

Synthesis of enantioenriched sulfoxides

O’Mahony¹,

Kelly²,

Lawrence³

et al. 2011

Arkivoc

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This review discusses strategies for the asymmetric synthesis of sulfoxides, compounds with many applications in stereoselective synthesis and in some cases with pharmaceutical application. The review describes asymmetric oxidation, including metal catalyzed and nonmetal and biological oxidation processes, in addition to synthetic approaches via nucleophilic substitution of appropriately substituted precursors. Kinetic resolution in oxidation of sulfoxides to the analogous sulfones is also discussed; in certain instances, access to enantioenriched sulfoxides can be achieved via a combination of asymmetric sulfide oxidation and complementary kinetic resolution in sulfoxide oxidation.

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“…One of the most convenient and straightforward protocols to generate the chiral sulfoxides is the asymmetric oxidation of sulfides. To date, the most efficient and successful protocols for the asymmetric sulfoxidation include the modified Sharpless procedures and oxidation using the stoichiometric quantity of enantiomerically pure Davis reagents or oxaziridinium salts [ 4 , 36 , 37 , 38 ]. However, asymmetric catalytic sulfoxidation, by comparison, has been less explored.…”

Section: Asymmetric Oxidation Of Oxaziridinesmentioning

confidence: 99%

Recent Advances in the Catalytic Asymmetric Reactions of Oxaziridines

et al. 2018

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Oxaziridines have emerged as powerful and elegant oxygen- and nitrogen-transfer agents for a broad array of nucleophiles, due to the remarkably high and tunable reactivities. However, the asymmetric catalysis involving oxaziridines is still in its infancy. Herein, this review aims to examine recent advances in the catalytic asymmetric transformations of oxaziridines, including oxidation, amination, cycloaddition and deracemization.

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Chemistry of oxaziridines. 8. Asymmetric oxidation of nonfunctionalized sulfides to sulfoxides with high enantioselectivity by 2-sulfamyloxaziridines. Influence of the oxaziridine C-aryl group on the asymmetric induction

Cited by 82 publications

References 0 publications

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Synthesis of enantioenriched sulfoxides

Recent Advances in the Catalytic Asymmetric Reactions of Oxaziridines

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