592-70-1Relevant academic research and scientific papers
α-Nitrosostyrenes as Three-Atom Units for the (3+1) Cyclization Reaction: Facile Access to 2,3-Dihydrodiazete N-Oxides and Their Diversified Synthetic Conversions
Shen, Li-Wen,Wang, Zhen-Hua,You, Yong,Yuan, Wei-Cheng,Zhao, Jian-Qiang,Zhou, Ming-Qiang
supporting information, p. 1094 - 1099 (2022/02/10)
An unprecedented (3+1) cyclization of α-nitrosostyrenes, generated in situ from α-bromooximes, and N-tosyloxycarbamates was developed, which enables the synthesis of a range of structurally unique and hitherto unexplored 2,3-dihydrodiazete N-oxides in mod
Synthesis of oxazolidinones: Rhodium-catalyzed C-H amination of: N -mesyloxycarbamates
Lebel, Hélène,Mamani Laparra, Laura,Khalifa, Maroua,Trudel, Carl,Audubert, Clément,Szponarski, Mathieu,Dicaire Leduc, Cédric,Azek, Emna,Ernzerhof, Matthias
supporting information, p. 4144 - 4158 (2017/07/10)
N-Mesyloxycarbamates undergo intramolecular C-H amination reactions to afford oxazolidinones in good to excellent yields in the presence of rhodium(ii) carboxylate catalysts. The reaction is performed under green conditions and potassium carbonate is used, forming biodegradable potassium mesylate as a reaction by-product. This method enables the production of electron-rich, electron-deficient, aromatic and heteroaromatic oxazolidinones in good to excellent yields. Conformationally restricted cyclic secondary N-mesyloxycarbamates furnish cis-oxazolidinones in high yields and selectivity; DFT calculations are provided to account for the observed selectivity. trans-Oxazolidinones were prepared from acyclic secondary N-mesyloxycarbamates using Rh2(oct)4. The selectivity was reverted with a cytoxazone N-mesyloxycarbamate precursor using large chiral rhodium(ii) carboxylate complexes, affording the corresponding cis-oxazolidinone. This orthogonal selectivity was used to achieve the formal synthesis of (-)-cytoxazone.
Regioselective Synthesis of 2-Vinylanilines Using O-aroyloxycarba-mates by Sequential Decarboxylation/Amination/Heck Reaction
Li, Peihe,Ma, Nuannuan,Li, Jikun,Wang, Zheng,Dai, Qipu,Hu, Changwen
, p. 8251 - 8257 (2017/08/14)
A new sequential approach for 2-vinylanilines utilizing aryl carboxylic acids as stable, inexpensive and widely available arylating reagents is described. Employing a Pd-POVs catalyst system, this protocol is not only overcoming the restriction barrier of decarboxylative coupling to ortho-substituted substrates, but also provides site-special to create new C(sp2)-N and C(sp2)-C(sp2) bonds. Mechanistic experiments suggest the cleavage of C(sp2)-COOH gives priority to C(sp2)-X bond in this reaction.
N-tosyloxycarbamates as a source of metal nitrenes: Rhodium-catalyzed C-H insertion and aziridination reactions
Lebel, Helene,Huard, Kim,Lectard, Sylvain
, p. 14198 - 14199 (2007/10/03)
The rhodium-catalyzed decomposition of N-tosyloxycarbamates to generate metal nitrenes which undergo intramolecular C-H insertion or aziridination reaction is described. Aliphatic N-tosyloxycarbamates produce oxazolidinones with high yields and stereospecificity through insertion in benzylic, tertiary, and secondary C-H bonds. Intramolecular aziridination occurs with allylic N-tosyloxycarbamates to produce aziridines as single diastereomers. The reaction proceeds at room temperature using a rhodium catalyst and an excess of potassium carbonate and does not require the use of strong oxidant, such as hypervalent iodine reagents. A rhodium nitrene species is presumably involved, as both reactions are stereospecific. Copyright
