Rhodium(II)-catalyzed aziridinations and CH insertions with [N-(p-nitrobenzenesulfonyl)imino]phenyliodinane

Müller, Paul; Baud, Corine; Jacquier, Yvan Daniel Michel; Moran, M.; Nägeli, Ivo

doi:10.1002/(sici)1099-1395(199606)9:6<341::aid-poc791>3.0.co;2-5

Cited by 93 publications

(53 citation statements)

References 31 publications

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“…45 Müller utilized Rh 2 (R-BNP) 4 (29a) in the asymmetric aziridination of styrenes and achieved 73% ee with cis-β-methylstyrene 31 (Scheme 7). 46 Hodgson successfully employed Rh 2 (R-DDBNP) 4 (34d) in an ylide-mediated intramolecular cycloaddition of 33, which afforded 34 in 81% yield and 88% ee (Scheme 8). 45…”

Section: Dirhodium (Ii) Phosphonatessupporting

confidence: 68%

High symmetry dirhodium(II) paddlewheel complexes as chiral catalysts

Hansen

Davies

2008

Coordination Chemistry Reviews

233

150

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The design and use of chiral dirhodium(II) paddlewheel complexes as catalysts for asymmetric metal carbenoid and metal nitrenoid reactions, and as Lewis acids have become areas of considerable interest during the past two decades. The metal carbenoid chemistry is especially versatile, encompassing transformations such as C-H insertions, cyclopropanations and ylide formation. A number of different classes of dirhodium(II) catalysts have been found to be broadly effective in this chemistry. This review will highlight that many of these catalysts have higher symmetry than the individual chiral ligands themselves. An introduction of theoretical aspects concerning the structure and symmetry of chiral dirhodium(II) complexes will be given followed by an overview of the major classes of catalysts developed to date. Some representative examples of the synthetic potential of these catalysts will also be discussed.

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Section: Dirhodium (Ii) Phosphonatessupporting

confidence: 68%

High symmetry dirhodium(II) paddlewheel complexes as chiral catalysts

Hansen

Davies

2008

Coordination Chemistry Reviews

233

150

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“…Intermolecular amination experiments described by Müller using O 2 NC 6 H 4 SO 2 N=IPh (NsN=IPh) as the nitrene source underscore the value of certain rhodium(II) catalysts for C-H insertion (Scheme 17.5) [12,[34][35][36]. In accord with Breslow's finding, dirhodium carboxylates were demonstrated to catalyze the amination of allylic, benzylic, and adamantyl substrates.…”

Section: Intermolecular C-h Amination With Rhodium(ii) Catalystsmentioning

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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“…Mn(III) -, Fe(III) -, or Rh(II) -catalyzed intra -and intermolecular C -H insertions has been achieved with tosylimidophenyliodinane 184 [251] . Effective intermolecular C -H amination was later demonstrated by Muller and others using p -nitrophenylsulfonyl imidoiodinane 185 [71,75,77] . This class remains the most widely used among nitrene precursors.…”

Section: Generation Of Metal Nitrenoids and Their Reactionsmentioning

confidence: 61%

“…C -H amination via the intermediate metal nitrenoid species often competes with aziridination, but upon using electron -defi cient ruthenium [243,244,247,253,257,258] , manganese [78,243,249,250,253,259,260] , and rhodium [71,77,248,261,262] porphyrin complexes, exclusive C -H amination has been observed [251] . Metal porphyrin -catalyzed C -H amination has been attempted with benzylic, allylic, and hydrocarbon systems with arylimidoiodinanes as nitrene sources [249,251] .…”

Section: R U ( II ) and M N ( Iii ) Porphyrin Complexesmentioning

confidence: 99%