Cargando…

Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams

A palladium(ii)-catalysed C(sp(3))–H carbonylation of free(NH) secondary aliphatic amines to 2-pyrrolidinones is described. A correlation between the nature of the carboxylate ligand and the diastereoselectivity and yield of the process was observed. As such, under these optimal conditions a range o...

Descripción completa

Detalles Bibliográficos
Autores principales:	Png, Zhuang Mao, Cabrera-Pardo, Jaime R., Peiró Cadahía, Jorge, Gaunt, Matthew J.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	Royal Society of Chemistry 2018
Materias:	Chemistry
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6182607/ https://www.ncbi.nlm.nih.gov/pubmed/30393523 http://dx.doi.org/10.1039/c8sc02855a

Ejemplares similares

Cobalt-catalysed C–H carbonylative cyclisation of aliphatic amides
por: Williamson, Patrick, et al.
Publicado: (2017)

One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles
por: Lu, Juan, et al.
Publicado: (2022)

Diastereoselective Synthesis of γ- and δ-Lactams from Imines and Sulfone-Substituted Anhydrides
por: Sorto, Nohemy A., et al.
Publicado: (2014)

Diastereoselective Synthesis of N-Methylspiroindolines by Intramolecular Mizoroki–Heck Annulations
por: Lindman, Jens, et al.
Publicado: (2022)

Cascade annulation reaction (CAR): highly diastereoselective synthesis of pyranopyrazole scaffolds
por: Bakthadoss, Manickam, et al.
Publicado: (2020)

Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp(3))–H bonds of aliphatic amine substrates
por: Wang, Chao, et al.
Publicado: (2015)

Diastereoselective Synthesis of Potent Antimalarial Cis-β-lactam Agents
por: Jarrahpour, Aliasghar, et al.
Publicado: (2019)

A general carbonyl alkylative amination for tertiary amine synthesis facilitated by visible light
por: Kumar, Roopender, et al.
Publicado: (2020)

Ligand-assisted palladium-catalyzed C–H alkenylation of aliphatic amines for the synthesis of functionalized pyrrolidines
por: He, Chuan, et al.
Publicado: (2017)

Intermolecular diastereoselective annulation of azaarenes into fused N-heterocycles by Ru(II) reductive catalysis
por: Zhao, He, et al.
Publicado: (2022)

From Racemic Alcohols to Enantiopure Amines: Ru-Catalyzed Diastereoselective Amination
por: Oldenhuis, Nathan J., et al.
Publicado: (2014)

Asymmetric Redox-Annulation of Cyclic Amines
por: Kang, YoungKu, et al.
Publicado: (2015)

Traceless Redox-Annulations of Alicyclic Amines
por: Rickertsen, Dillon R. L., et al.
Publicado: (2020)

BF(3)·Et(2)O-Mediated annulation of α-keto acids with aliphatic ketones for the synthesis of γ-hydroxy-butenolides and γ-alkylidene-butenolides
por: Cheng, Zhenfeng, et al.
Publicado: (2022)

Diastereoselective functionalisation of benzo-annulated bicyclic sultams: Application for the synthesis of cis-2,4-diarylpyrrolidines
por: Kelleher, Susan, et al.
Publicado: (2009)

Redox-Annulation of Cyclic Amines and β-Ketoaldehydes
por: Chen, Weijie, et al.
Publicado: (2016)

Carbonyl-to-nickel exchange on a lactam skeleton
por: Guo, Huijuan
Publicado: (2023)

Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams
por: Byrd, Katherine M
Publicado: (2015)

Diastereoselective Synthesis of β-Lactams by Ligand-Controlled Stereodivergent Intramolecular Tsuji–Trost Allylation
por: Faltracco, Matteo, et al.
Publicado: (2020)

Synthesis of Polycyclic Imidazolidinones via Amine Redox-Annulation
por: Zhu, Zhengbo, et al.
Publicado: (2017)

Multicomponent Domino Cyclization of Ethyl Trifluoropyruvate with Methyl Ketones and Amino Alcohols as A New Way to γ-Lactam Annulated Oxazacycles
por: Goryaeva, Marina V., et al.
Publicado: (2023)

Practical, Asymmetric Route to Sitagliptin and Derivatives: Development and Origin of Diastereoselectivity
por: Gutierrez, Osvaldo, et al.
Publicado: (2015)

Total Synthesis of Tetrahydrolipstatin and Stereoisomers via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic Alcohols
por: Mulzer, Michael, et al.
Publicado: (2014)

Selectivity of Copper by Amine-Based Ion Recognition Polymer Adsorbent with Different Aliphatic Amines
por: Othman, Nor Azillah Fatimah, et al.
Publicado: (2019)

Catalytic Generation and Use of Ketyl Radical from Unactivated Aliphatic Carbonyl Compounds
por: Seo, Hyowon, et al.
Publicado: (2019)

Visible-light mediated carbonyl trifluoromethylative amination as a practical method for the synthesis of β-trifluoromethyl tertiary alkylamines
por: Kolahdouzan, Kavoos, et al.
Publicado: (2020)

Amine dehydrogenases: efficient biocatalysts for the reductive amination of carbonyl compounds
por: Knaus, Tanja, et al.
Publicado: (2017)

Cooperative Catalysis by Carbenes and Lewis Acids in a Highly Stereoselective Route to γ-Lactams
por: Raup, Dustin E. A., et al.
Publicado: (2010)

Scandium-catalysed intermolecular hydroaminoalkylation of olefins with aliphatic tertiary amines
por: Nako, Adi E., et al.
Publicado: (2016)

Synthesis, characterization and applications of poly-aliphatic amine dendrimers and dendrons
por: Gillani, Syeda Shaista, et al.
Publicado: (2020)

Quantum Chemical Analysis of the Corrosion Inhibition Potential by Aliphatic Amines
por: Malinowski, Szymon, et al.
Publicado: (2021)

Mechanistic Aspects of the Electrochemical Oxidation of Aliphatic Amines and Aniline Derivatives
por: Mruthunjaya, Ashwin K. V., et al.
Publicado: (2023)

Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams
por: Kalaitzakis, Dimitris, et al.
Publicado: (2018)

Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes
por: Dong, Taiwei, et al.
Publicado: (2021)

cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent
por: Filatov, Vadim E., et al.
Publicado: (2021)

Site-selective, catalytic, and diastereoselective sp(3) C–H hydroxylation and alkoxylation of vicinally functionalized lactams
por: Beng, Timothy K., et al.
Publicado: (2020)

Eco-friendly Route for Thermoplastic Polyurethane Elastomers with Bio-based Hard Segments Composed of Bio-glycol and Mixtures of Aromatic–Aliphatic and Aliphatic–Aliphatic Diisocyanate
por: Głowińska, Ewa, et al.
Publicado: (2021)

Total Synthesis of Eliglustat via Diastereoselective Amination of Chiral para-Methoxycinnamyl Benzyl Ether
por: Kong, Younggyu, et al.
Publicado: (2022)

Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ‐Lactams
por: Sietmann, Jan, et al.
Publicado: (2021)

Diastereoselective synthesis of CF(3)-dihydrobenzofurans by [4+1] annulation of in situ-generated CF(3)-o-quinone methides and sulfur ylides
por: Jha, Babli K., et al.
Publicado: (2020)

Cannot write session to /tmp/vufind_sessions/sess_mlt71thv10286hjjtjvgo863f5