Halocyclizations of Unsaturated Sulfoximines

Wang, Han; Frings, Marcus; Bolm, Carsten

doi:10.1021/acs.orglett.6b00958

Cited by 59 publications

(27 citation statements)

References 43 publications

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“…1 With reference to NH--sulfoximines, the availability of a free nitrogen group offers the possibility to further functionalize a molecule. Methodologies for N--trifluoromethylation, 8 trifluoromethylthiolation, 9 aroylation, 10 intramolecular halocyclization, 11 alkynylation, 12 and alkylation, 13 have increased the available molecular diversity in compounds bearing the sulfoximine group. Very recently, an interesting preparation of optically active of NH--sulfoximines via organocatalytic kinetic resolution has been reported.…”

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confidence: 99%

Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

et al. 2017

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Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

et al. 2017

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“…Bolm and co‐workers further extended their methodology to the synthesis of simple five‐membered ring systems of novel isothiazole oxides (Scheme ) . Two approaches were pursued based on (i) intramolecular halocyclization of unsaturated sulfoximines using iodobenzene diacetate as an oxidant (Scheme A) and (ii) an iodine‐mediated HLF (HLF=Hofmann–Löffler‐.Freytag) reaction of sulfoximines (Scheme B) . These methods exploit the nucleophilic interaction of the sulfoximine nitrogen atom with a halonium ion and benzylic cation, respectively, to afford non‐benzofused isothiazole oxides in high yields.…”

Section: Synthesis Of Isothiazolesmentioning

confidence: 99%

Recent Advances in the Synthesis and Reactivity of Isothiazoles

2019

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Isothiazoles represent an important class of five‐membered sulfur heterocycles that are widely utilized in medicinal chemistry and organic synthesis due to the unique properties of two electronegative heteroatoms in a 1,2‐relationship. However, in contrast to other 1,2‐azoles, the facile assembly of isothiazoles has always been considered a substantial challenge. In the last decade, major advances have taken place in the fields of synthesis and functionalization of isothiazoles that make them accessible to a wide range of interested chemists through unprecedented pathways. New condensation methods have emerged that address the challenges posed by unstable thiohydroxylamine. New metal‐catalyzed approaches have been reported that deliver densely decorated isothiazoles bearing various sensitive functional groups. New functionalization strategies have been developed through both cross‐coupling and direct C−H activation chemistry. Finally, the emergence of novel heterocyclic architectures based on isothiazole opens the door for future investigations of this versatile heterocyclic scaffold. This review covers the period from January 2004 to December 2018 and is intended as a sequel to the review on isoxazoles, which represent another class of synthetically‐important 1,2‐azoles (see Adv. Synth. Catal. 2015, 357, 2583–2614).

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“…In this case, elemental iodine is most commonly used as the halogenating agent in the presence of NaHCO 3 or K 2 CO 3 , 28,29 N-bromosuccinimide (NBS) 30 or N-iodosuccinimide (NIS). 31 Another approach involves the use of an oxidant and a halogen source: (diacetoxyiodo)benzene PhI(OAc) 2 (PIDA)/KI, 32,33 HF/Py, 34 Oxone ® (potassium monopersulfate)/RI 35 or KBr, 36 tBuOCl/NaI, 37 chloramine-T (CT)/I 2 , 38,39 and Cu(OTf) 2 /iPrI. 40 In some cases, high selectivities of haloamination were achieved by carrying out the reactions in the presence of transition-metal salts.…”

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Synthesis of 3-Iodomethyl Sultams

Filimonchuk

Nazarenko

Shvydenko

et al. 2020

Synlett

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A method for the synthesis of iodomethyl-substituted five-membered sultams has been developed. The sultams were synthesized by intramolecular iodoamination of alkenyl sulfamides. The method allows synthesis of N- and C-substituted sultams. NH-Sultams were prepared by acidic cleavage of the corresponding tert-butyl sultams that are readily available. Varying the length of alkenyl substituent at sulfamide it was shown that only five- and six-membered sultams could be prepared by this method. Neither four- nor seven-membered sultams were detected. The simple practical procedure and available starting materials make the variously substituted sultams readily available.

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Halocyclizations of Unsaturated Sulfoximines

Cited by 59 publications

References 43 publications

Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

Recent Advances in the Synthesis and Reactivity of Isothiazoles

Synthesis of 3-Iodomethyl Sultams

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