Synthesis of 1,2,5-thiadiazolidin-3-one 1,1-dioxides: x-ray structure determination of 4,4-diphenyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Timberlake, Jack W.; Ray, Warren J.; Stevens, Edwin D.; Klein, Cheryl L.

doi:10.1021/jo00285a035

Cited by 27 publications

(13 citation statements)

References 4 publications

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“…Sulfamates are readily accessed from 18 and 28 alcohols (for example, 31) using ClSO 2 NH 2 , a convenient reagent that is prepared from inexpensive ClSO 2 NCO and HCO 2 H [70,71]. These compounds are often crystalline and, as with carbamate esters, are stable to prolonged storage.…”

Section: Sulfamate Estersmentioning

confidence: 99%

Rhodium(II)‐Catalyzed Oxidative Amination

Espino

Bois

2005

Modern Rhodium‐Catalyzed Organic Reactions

105

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17 Rhodium(II)-Catalyzed Oxidative Amination 380 Scheme 17.1 Copper-catalyzed decomposition of arylsulfonyl azides. Scheme 17.2 Intramolecular C-H amination of an iminoiodinane. 17.3 Intermolecular C-H Amination with Rhodium(II) Catalysts 381 Scheme 17.3 Metal porphyrin-catalyzed allylic amination. Scheme 17.4 C-H amination by a radical-rebound mechanism. 17 Rhodium(II)-Catalyzed Oxidative Amination 382 Scheme 17.5 Rhodium-catalyzed N-atom transfer using NsN=IPh. Scheme 17.6 Stereospecific C-H amination under rhodium-catalyzed conditions. 17.3 Intermolecular C-H Amination with Rhodium(II) Catalysts 383 Scheme 17.7 Radical clock study of metallo-nitrene C-H insertion. Scheme 17.8 Intermolecular C-H insertion by chiral rhodium catalysts. 17.5 Intramolecular C-H Amination with Rhodium(II) Catalysts 385 Scheme 17.11 Allylic and benzylic amination using PhI(OAc) 2 . 17.5 Intramolecular C-H Amination with Rhodium(II) Catalysts 387 Tab. 17.1 C-H amination of 18 carbamate esters. Entry Substrate Product Entry Substrate Product 17.5 Intramolecular C-H Amination with Rhodium(II) Catalysts 389 Scheme 17.14 Ketone formation by 28 alcohol-derived carbamates. 17.7 Enantioselective C-H Insertion with Sulfamate Esters 401 Scheme 17.29 Oxidative cyclization of unsaturated sulfonamides. Scheme 17.30 Preliminary investigations of asymmetric C-H amination. 17.11 Applications of C-H Amination in Synthesis 407 17.11 Applications of C-H Amination in Synthesis 409 Scheme 17.39 Asymmetric synthesis of (-)-tetrodotoxin. 17 Rhodium(II)-Catalyzed Oxidative Amination 410 Scheme 17.40 Nucleophilic ring opening of N-acylated oxathiazinanes. Scheme 17.41 Nickel-catalyzed cross-coupling of phenol-derived sulfamate esters.

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Section: Sulfamate Estersmentioning

confidence: 99%

Rhodium(II)‐Catalyzed Oxidative Amination

Espino

Bois

2005

Modern Rhodium‐Catalyzed Organic Reactions

105

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“…Treatment of amine (+)- 7a with chlorosulfonic acid followed by addition of sodium carbonate afforded the corresponding sodium sulfamate salt (+)- 12 . 11a Sequential in situ activation of 12 to form the sulfamoyl chloride 13 , followed by direct union with complex amine 7b provided the unsymmetrical sulfamide (+)- 6b (86%, based on 7b , Scheme 3). Exposure of the sulfamide (+)- 6b to N -chlorosuccinimide provided the corresponding unsymmetrical diazene 5b , likely via the transient thiadiaziridine dioxide 14b .…”

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confidence: 99%

Directed Heterodimerization: Stereocontrolled Assembly via Solvent-Caged Unsymmetrical Diazene Fragmentation

2011

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“…[7] For the purpose of orthogonal protection of the amino acids' catechol, the remaining phenol was TBS-protected to yield 10a. Subsequent hydroboration with oxidative work up gave the corresponding alcohol, which was sulfamoylated with in situ formed sulfamoyl chloride [8] 11 to furnish sulfamate 12a in 49 % yield on gram-scale starting from eugenol (7). Cramer's synthesis of fijiolide A (2a) demonstrated that the best atropselectivities in the cyclophane formation were obtained with the unprotected catechol.…”

Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis of the β‐Amino Acid Moiety of Fijiolide A

et al. 2018

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An enantioselective synthesis of the β‐amino acid moiety of fijiolide A is described. Starting from eugenol, two sulfamates could be obtained on gram scale as substrates for an enantioselective C–H amination using Rh2(R/S‐nap)4. Acylation and ring opening of the resulting oxathiazinanes, followed by stepwise oxidation of the corresponding amino alcohol and TES‐protection of the catechol gave rise to Cramer's amino acid fragment from the total synthesis of fijiolide A.

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Synthesis of 1,2,5-thiadiazolidin-3-one 1,1-dioxides: x-ray structure determination of 4,4-diphenyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Cited by 27 publications

References 4 publications

Rhodium(II)‐Catalyzed Oxidative Amination

Rhodium(II)‐Catalyzed Oxidative Amination

Directed Heterodimerization: Stereocontrolled Assembly via Solvent-Caged Unsymmetrical Diazene Fragmentation

Stereoselective Synthesis of the β‐Amino Acid Moiety of Fijiolide A

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