ChemInform Abstract: Stereoselective Synthesis of Allylic Sulfoximines from S‐(Chloromethyl)‐N‐methyl‐S‐phenylsulfoximine and Alkenyl Cuprates.

Bosshammer, S.; Gais, Hans‐Joachim

doi:10.1002/chin.199821088

Cited by 4 publications

(4 citation statements)

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“…The reaction conditions described by Bolm et al for nonfluorinated sulfoximines were also considered and gave rise to a small amount of derivative 4a with a mixture of unidentified fluorinated products (Table , entry 2) . The conditions of Grela et al allowed the formation of target 4a in acceptable yield (45 %) in a mixture with the S ‐phenyl sulfoximine 1′ (Table , entry 3) . Finally, an adaptation of the previous conditions allowed complete conversion and provided 4a in 78 % yield, with a reduced portion of de‐iodinated sulfoximine 1′ (Table , entry 4).…”

Section: Resultsmentioning

confidence: 99%

Facile Preparation of Vinyl S‐Trifluoromethyl NH Aryl Sulfoximines

et al. 2018

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We report herein the preparation of ortho‐vinylaryl S‐trifluoromethylated sulfoximines through cross‐coupling reactions. Two efficient palladium‐catalyzed procedures (Stille and Suzuki) were developed, with use of ortho‐iodo aryl sulfoximines as substrates, to give various vinyl derivatives in good yields. The difference in reactivity of the fluorinated derivatives, compared to nonfluorinated counterparts, allowed the use of free NH sulfoximines in the coupling processes, where they proved to be inert to cyclization. Finally, further transformations have been explored, such as metathesis coupling reactions, after post‐functionalization of the nitrogen atom by another vinyl group.

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Section: Resultsmentioning

confidence: 99%

Facile Preparation of Vinyl S‐Trifluoromethyl NH Aryl Sulfoximines

et al. 2018

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“…Owing to the interest of heterocyclic compounds in medicinal chemistry, different strategies to access cyclic sulfoximines have also been developed, especially for the synthesis of 6‐membered and benzo‐fused derivatives . The preparation of 5‐membered cyclic sulfoximines remains less explored and their synthesis in enantiopure form is limited to rather rare examples ,,,…”

Section: Figurementioning

confidence: 99%

Accessing Enantiopure Endocyclic Sulfoximines Through Catalytic Cycloisomerization of Oxygenated Propargyl‐Sulfinamides

et al. 2019

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In this study, a novel strategy to access endocyclic sulfoximines in an enantiopure form is reported. The approach is based on a silver nitratecatalyzed cyclo-isomerization reaction of oxygenated propargylic sulfinamides and provides efficiently 5-membered endocyclic sulfoximines (isothiazole 1-oxide). These new heterocyclic scaffolds can be isolated or directly converted into cyclic sulfinamides via Lewis acid-mediated sulfur dealkylation reactions.

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“…In the light of this continuous interest in the HLF reaction and based on our long‐lasting sulfur chemistry program, we wondered if appropriately substituted sulfoximine derivatives would also undergo HLF‐type cyclization reactions opening a straightforward access to synthetically interesting dihydroisothiazole oxides 2 . Considering previous reports, the iodine strategy appeared most attractive for the envisaged transformation, and S ‐phenyl‐ S ‐phenylpropyl sulfoximine ( 1 a ) was chosen as representative substrate of the initial experiments .…”

Section: Optimization Of the Reaction Conditions[a]mentioning

confidence: 99%