Cargando…

Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Lactams: Enantioselective Construction of All-Carbon Quaternary Stereocenters in Saturated Nitrogen-Containing Heterocycles

[Image: see text] Stereogenic nitrogen-containing heterocycles are ubiquitous in natural products and pharmaceutical compounds, but methods for their enantioselective construction have remained elusive. We report a general method for the asymmetric conjugate addition of arylboronic acids to β-alkyl/...

Descripción completa

Detalles Bibliográficos
Autores principales:	Zhang, Tianyi, Nishiura, Yuji, Cusumano, Alexander Q., Stoltz, Brian M.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2023
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10496148/ https://www.ncbi.nlm.nih.gov/pubmed/37639656 http://dx.doi.org/10.1021/acs.orglett.3c02064

Ejemplares similares

Enantioselective Construction of Quaternary N-Heterocycles by Palladium-Catalyzed Decarboxylative Allylic Alkylation of Lactams
por: Behenna, Douglas C., et al.
Publicado: (2011)

Enantioselective Construction of Remote Quaternary Stereocenters
por: Mei, Tian-Sheng, et al.
Publicado: (2014)

Catalytic enantioselective construction of vicinal quaternary carbon stereocenters
por: Zhou, Feng, et al.
Publicado: (2020)

Highly Enantioselective Iridium(I)‐Catalyzed Hydrocarbonation of Alkenes: A Versatile Approach to Heterocyclic Systems Bearing Quaternary Stereocenters
por: Arribas, Andrés, et al.
Publicado: (2021)

Origins of Enhanced Enantioselectivity in the Pd-Catalyzed Decarboxylative Allylic Alkylation of N-Benzoyl Lactams ()
por: Cusumano, Alexander Q., et al.
Publicado: (2023)

Enantioselective 1,3-Dipolar Cycloadditions of α-Methylene Lactams to Construct Spirocycles
por: Nishiura, Yuji, et al.
Publicado: (2023)

Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter
por: Franco, Francesca, et al.
Publicado: (2022)

Asymmetric construction of acyclic quaternary stereocenters via direct enantioselective additions of α-alkynyl ketones to allenamides
por: Wang, Jiawen, et al.
Publicado: (2021)

Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones
por: Boeser, Cornelia L., et al.
Publicado: (2015)

Catalytic enantioselective synthesis of fluoromethylated stereocenters by asymmetric hydrogenation
por: Yang, Jianping, et al.
Publicado: (2022)

Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters
por: Patel, Kaushalendra, et al.
Publicado: (2022)

Enantioselective Synthesis of α-Quaternary Mannich Adducts by Palladium-Catalyzed Allylic Alkylation: Total Synthesis of (+)-Sibirinine
por: Numajiri, Yoshitaka, et al.
Publicado: (2015)

Enantioselective Synthesis of Aza-Flavanones with an All-Carbon Quaternary Stereocenter via NHC-Catalyzed Intramolecular Annulation
por: Barańska, Izabela, et al.
Publicado: (2023)

Stereocontrolled access to δ-lactone-fused-γ-lactams bearing angular benzylic quaternary stereocenters
por: Beng, Timothy K., et al.
Publicado: (2022)

Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters
por: Li, Zhiyang, et al.
Publicado: (2021)

Enantioselective synthesis of cis-hydrobenzofurans bearing all-carbon quaternary stereocenters and application to total synthesis of (‒)-morphine
por: Zhang, Qing, et al.
Publicado: (2019)

Cross-dehydrogenative coupling enables enantioselective access to CF(3)-substituted all-carbon quaternary stereocenters
por: Pan, Xiaoguang, et al.
Publicado: (2020)

Enantioselective construction of triaryl-substituted all-carbon quaternary stereocenters via organocatalytic arylation of oxindoles with azonaphthalenes
por: Chen, Pengquan, et al.
Publicado: (2023)

Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four Consecutive Stereocenters and Quaternary α-Nitro Esters via Organocatalytic Enantioselective Michael–Michael Cascade Reactions
por: Chaudhari, Prakash D., et al.
Publicado: (2019)

Palladium-catalyzed enantioselective Heck alkenylation of trisubstituted allylic alkenols: a redox-relay strategy to construct vicinal stereocenters
por: Zhang, Chun, et al.
Publicado: (2017)

Stereodivergent synthesis of vicinal quaternary-quaternary stereocenters and bioactive hyperolactones
por: Zheng, Haifeng, et al.
Publicado: (2018)

Nickel-catalyzed enantioselective α-heteroarylation of ketones via C–F bond activation to construct all-carbon quaternary stereocenters
por: Gu, Xiaodong, et al.
Publicado: (2022)

Enantioselective synthesis of highly oxygenated acyclic quaternary center-containing building blocks via palladium-catalyzed decarboxylative allylic alkylation of cyclic siloxyketones
por: Ngamnithiporn, Aurapat, et al.
Publicado: (2020)

Construction of polycyclic structures with vicinal all-carbon quaternary stereocenters via an enantioselective photoenolization/Diels–Alder reaction
por: Hou, Min, et al.
Publicado: (2021)

Enantioselective [3+2]-cycloaddition of 2,3-disubstituted cyclobutenones: vicinal quaternary stereocenters construction and skeletal functionalization
por: Lu, Licheng, et al.
Publicado: (2023)

Palladium-Catalyzed Stereoselective Construction of 1,3-Stereocenters Displaying Axial and Central Chirality via Asymmetric Alkylations
por: Xue, Aiqi, et al.
Publicado: (2023)

Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones
por: Craig, Robert A., et al.
Publicado: (2015)

Biocatalytic Conversion of Cyclic Ketones Bearing α‐Quaternary Stereocenters into Lactones in an Enantioselective Radical Approach to Medium‐Sized Carbocycles
por: Morrill, Charlotte, et al.
Publicado: (2018)

Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters
por: Liu, Ren-Rong, et al.
Publicado: (2017)

Enantioselective Synthesis of Acyclic Orthogonally Functionalized Compounds Bearing a Quaternary Stereocenter Using Chiral Ammonium Salt Catalysis
por: Röser, Katharina, et al.
Publicado: (2021)

Recent advances in palladium-catalysed asymmetric 1,4–additions of arylboronic acids to conjugated enones and chromones
por: Bartáček, Jan, et al.
Publicado: (2021)

Catalytic enantioselective synthesis of tetrasubstituted chromanones via palladium-catalyzed asymmetric conjugate arylation using chiral pyridine-dihydroisoquinoline ligands
por: Baek, Doohyun, et al.
Publicado: (2020)

Palladium-catalyzed asymmetric three-component reaction between glyoxylic acid, sulfonamides and arylboronic acids for the synthesis of α-arylglycine derivatives
por: Jakob, Bastian, et al.
Publicado: (2023)

Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization
por: Wang, Qiang, et al.
Publicado: (2020)

Organocatalytic enantioselective S(N)1-type dehydrative nucleophilic substitution: access to bis(indolyl)methanes bearing quaternary carbon stereocenters
por: Zhu, Wen-Run, et al.
Publicado: (2021)

Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
por: Ngamnithiporn, Aurapat, et al.
Publicado: (2018)

Asymmetric Construction of All-Carbon Quaternary Stereocenters by Chiral-Auxiliary-Mediated Claisen Rearrangement and Total Synthesis of (+)-Bakuchiol
por: Takao, Ken-ichi, et al.
Publicado: (2012)

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

Quaternary Stereocenters via an Enantioconvergent Catalytic S(N)1 Reaction
por: Wendlandt, Alison E., et al.
Publicado: (2018)

Palladium(ii)-catalyzed γ-selective hydroarylation of alkenyl carbonyl compounds with arylboronic acids
por: Matsuura, Rei, et al.
Publicado: (2018)

Cannot write session to /tmp/vufind_sessions/sess_3bvb0j3stipc7gmp5mjpk59u4s