A study of the functional group compatibility of sulfoximination methods

Cren, Sylvaine; Kinahan, Taryn C.; Skinner, Catharine L.; Tye, Heather

doi:10.1016/s0040-4039(02)00378-7

Cited by 27 publications

(12 citation statements)

References 8 publications

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“…Since a free sulfonimide was required for further synthesis, the deprotection of 6b and 6c was then attempted. Conditions for the removal of the nosyl and SES groups have been developed by us in previous work [11]. Treatment of 6b with PhSH and Cs 2 CO 3 in MeCN resulted in formation of a complex mixture of products.…”

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confidence: 99%

Investigation of Synthetic Routes towards Derivatives of 3-(Phenylsulfonimidoyl)propanoic Acid

Tye

Skinner

2002

HCA

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Dedicated to Professor Dieter Seebach on the occasion of his 65th birthdayThe synthesis of a range of 3-(phenylsulfonimidoyl)propanoate derivatives is described. A number of strategies for the imination of the key sulfoxide methyl 3-(penylsulfinyl)propanoate are discussed including the use of O-(mesitylsulfonyl)hydroxylamine (MSH) and iminoiodane reagents (PhÀINÀSO 2 R). A successful strategy for the preparation of the target compounds was the use of MSH followed by in situ coupling with a NBoc-protected amino acid. The pseudo-dipeptides thus formed exhibited interesting conformational properties in CDCl 3 solution giving evidence of intramolecular H-bonds in all cases, except for the proline derivative.

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confidence: 99%

Investigation of Synthetic Routes towards Derivatives of 3-(Phenylsulfonimidoyl)propanoic Acid

Tye

Skinner

2002

HCA

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“…N ‐(4‐Nitrobenzenesulfonyl) methyl phenyl sulfoximine (2) :12, 14–17 Chromatography: gradient of ethyl acetate/pentane 1:2 to 1:1; pale yellow solid; m.p. 148–150 °C (lit.…”

Section: Methodsmentioning

confidence: 99%

“…At the same time, Müller reported that CuOTf was an efficient catalyst for sulfoxide iminations with PhINTs 9. Subsequently, we,10 Nakayama11 and Tye,12 published Cu I ‐catalyzed reactions with CuPF 6 , which proved to be a more efficient catalyst. Notably, Tye described the application of modified iminoiodinanes such as PhINNs (Ns= para ‐nitrobenzenesulfonyl) and PhINSes (Ses=trimethylsilylethylsulfonyl) having easily removable protecting groups.…”

Section: Introductionmentioning

confidence: 94%

Comparative Study of Metal‐Catalyzed Iminations of Sulfoxides and Sulfides

Mancheño

Bolm

2007

Chemistry A European J

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A comparative study of the imination of sulfur compounds with various metal catalysts in combination with isolated or in situ generated iminoiodinanes (PhI==NR) as nitrogen sources is presented. The influence of the metal catalyst towards the imination of a variety of substituted sulfoxides has been evaluated. Moreover, the effect of the different oxidation states of sulfur on the reactivity and selectivity of the nitrogen transfer redox process in the formation of sulfilimines and sulfoximines was studied. Depending on both the specific metal catalyst as well as the employed nitrene precursor, the sulfide/sulfoxide imination ratio varied in transformations of thianthrene-5-oxide and substituted para-thio phenylsulfoxides.

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“…Deprotecting the sulfoximine adducts with thiophenol (with R 3 =Ns, and p‐nosyl) or TBAF (with R 3 =Ses) gave NH‐sulfoximines (Scheme 2). [25] …”

Section: Syntheses Of Nh‐sulfoximinesmentioning

confidence: 99%

Syntheses and Transformations of Sulfoximines

Zheng

Chen

Feng

et al. 2020

The Chemical Record

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Sulfoximines are widely used as medicines, agricultural chemicals, chiral precursors, and chiral ligands in asymmetric synthesis, as well as pivotal intermediates for the construction of heterocyclic compounds. NH‐sulfoximines may be synthesized from thioethers, sulfoxides, sulfilimines, and sulfinamides. NH‐sulfoximines can undergo various transformations, such as arylations, alkylations, vinylations, and alkynylations. Here, we review the methods that have been applied to the syntheses and transformations of NH‐sulfoximines.

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A study of the functional group compatibility of sulfoximination methods

Cited by 27 publications

References 8 publications

Investigation of Synthetic Routes towards Derivatives of 3-(Phenylsulfonimidoyl)propanoic Acid

Investigation of Synthetic Routes towards Derivatives of 3-(Phenylsulfonimidoyl)propanoic Acid

Comparative Study of Metal‐Catalyzed Iminations of Sulfoxides and Sulfides

Syntheses and Transformations of Sulfoximines

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