Sulfonimidoyl chlorides by oxidation of sulfinamides with tert-butyl hypochlorite

Johnson, Carl R.; Wambsgans, Anthony

doi:10.1021/jo01327a051

Cited by 43 publications

(15 citation statements)

References 2 publications

(2 reference statements)

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“…Sulfinamides 51, which are easily prepared from sulfinyl chlorides 50 (X = Cl) (Scheme 9, Path A) and primary amines, can be oxidised employing different sources of electrophilic chlorine [104][105][106] (Path B). The most convenient reagent in this respect seems to be t-butyl hypochlorite introduced by Johnson in 1979.…”

Section: From Sulfonimidoyl Halogenides and Sulfonimidatesmentioning

confidence: 99%

Sulfoximines: Structures, Properties and Synthetic Applications

2000

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This review presents a comprehensive treatment of sulfoximine chemistry particularly emphasising synthetic developments and structural work after 1985. Following a brief introduction, the structures and properties of sulfoximines and metallated sulfoximines are discussed. The second section deals with the preparation of sulfoximines emphasising new methods. The main part of the review is concerned with reactions of sulfoximines. The material in this section is organised based on the reactivity pattern displayed by the various sulfoximines. Therefore they are grouped roughly into three classes of compounds. The first group of sulfoximines comprises compounds acting as C-nucleophiles, the second one contains electrophilic sulfoximines and the last group is made up of sulfoximines being useful as (chiral) ligands particularly for transition metals. Finally the ability of sulfoximines to act as "chiral chemical chameleons" and their rôle in biological and medicinal chemistry is briefly discussed.

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Section: From Sulfonimidoyl Halogenides and Sulfonimidatesmentioning

confidence: 99%

Sulfoximines: Structures, Properties and Synthetic Applications

2000

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“…Various mixtures of the configurationally stable epimeric sulfinamides 2 and epi-2 were oxidatively chlorinated at various temperatures in THF using tert-butyl hypochlorite as the reagent. [15] The resulting mixture of sulfonimidoyl chlorides 3 and epi-3 was transformed to the target sulfonimidates 1 and epi-1 by addition of a number of different nitrogen bases without prior isolation of the former compounds. From the results of these experiments we derived the scenario depicted in Scheme 1 (the bromine containing compounds 4 and epi-4 will be discussed later).…”

Section: Resultsmentioning

confidence: 99%

Cyclic Sulfonimidates by Dynamic Diastereomer-Differentiating Cyclisation: Large-Scale Synthesis and Mechanistic Studies

Reggelin

Junker

2001

Chem. Eur. J.

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A dynamic diastereomer differentiating cyclisation is the key step in a new large-scale synthesis of both enantiomers of the cyclic sulfonimidates 1 (Aldrich no. 54099-4) and ent-1 (Aldrich no. 54412-4). These are valuable starting materials in the asymmetric synthesis of chiral oxa- and azaheterocyclic compounds. NMR spectroscopic studies on the reacting system reveal N-chloro sulfinamides to be reactive intermediates in the oxidative chlorination of sulfinamides with tert-butyl hypochlorite and allow for the inspection of the configurational behaviour of the involved sulfonimidoyl chlorides and sulfonimidoyl bromides.

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“…N-Sulfinyltritylamine,T rNSO (6), showed undiminished reactivity after storage for four months in the freezer (À20 8 8C), and could be isolated on 10 gram scale in excellent yield. Furthermore,s ubsequent chlorination of the anionic sulfinamide intermediate with tert-butyl hypochlorite [19] proceeded with full conversion within fifteen minutes at the same temperature.T he use of N-chlorosuccinimide [7a] was also explored, but the reaction did not achieve completion even after five hours using 1.5 equivalents,while just 1.05 equivalents of tertbutyl hypochlorite proved sufficient. [18] Our efforts then turned to applying this rare example of as table sulfinylamine to our planned one-pot synthesis of sulfonimidamides.T he reaction of TrNSO with commercially available 4-fluorophenylmagnesium bromide in THF was selected for initial investigation.…”

Section: Sulfonamideshavearichhistoryinmedicinalchemistryandmentioning

confidence: 99%

One‐Pot, Three‐Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N‐Sulfinyltritylamine, TrNSO

2017

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Sulfonimidamides are increasingly important molecules in medicinal chemistry and agrochemistry, but their preparation requires lengthy synthetic sequences, which has likely limited their use. We describe a one-pot de novo synthesis of sulfonimidamides from widely available organometallic reagents and amines. This convenient and efficient process uses a stable sulfinylamine reagent, N-sulfinyltritylamine (TrNSO), available in one step on 10 gram scale, as a linchpin. In contrast to classical approaches starting from thiols or their derivatives, our TrNSO-based approach facilitates the rapid assembly of the three reaction components into a variety of differentially substituted sulfonimidamides containing medicinally relevant moieties, including pyridines and indoles. Analogues of the sulfonamide-containing COX-2 inhibitor Celecoxib were prepared and evaluated.

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Sulfonimidoyl chlorides by oxidation of sulfinamides with tert-butyl hypochlorite

Cited by 43 publications

References 2 publications

Sulfoximines: Structures, Properties and Synthetic Applications

Sulfoximines: Structures, Properties and Synthetic Applications

Cyclic Sulfonimidates by Dynamic Diastereomer-Differentiating Cyclisation: Large-Scale Synthesis and Mechanistic Studies

One‐Pot, Three‐Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N‐Sulfinyltritylamine, TrNSO

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