Cargando…

Enantioselective Annulations for Dihydroquinolones by in Situ Generation of Azolium Enolates

[Image: see text] A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide...

Descripción completa

Detalles Bibliográficos
Autores principales:	Lee, Anna, Younai, Ashkaan, Price, Christopher K., Izquierdo, Javier, Mishra, Rama K., Scheidt, Karl A.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2014
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120988/ https://www.ncbi.nlm.nih.gov/pubmed/25017004 http://dx.doi.org/10.1021/ja505880r

Ejemplares similares

Acyl Donor Intermediates in N‐Heterocyclic Carbene Catalysis: Acyl Azolium or Azolium Enolate?
por: Biswas, Animesh, et al.
Publicado: (2021)

Enantioselective palladium(0)-catalyzed intramolecular cyclopropane functionalization: access to dihydroquinolones, dihydroisoquinolones and the BMS-791325 ring system
por: Pedroni, J., et al.
Publicado: (2015)

Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions
por: Stockhammer, Lotte, et al.
Publicado: (2021)

Reversal of Enantioselectivity in the Conjugate Addition Reaction of Cyclic Enones with the CuOTf/Azolium Catalytic System
por: Nakano, Yuki, et al.
Publicado: (2021)

Carbene catalyzed umpolung of α,β-enals: a reactivity study of diamino dienols vs. azolium enolates, and the characterization of advanced reaction intermediates
por: Yatham, Veera Reddy, et al.
Publicado: (2015)

Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Cyclic Ketone Enolates: Synergetic Effect of Ligands and Barium Enolates
por: Chen, Wenyong, et al.
Publicado: (2014)

Phosphine-Catalyzed Enantioselective Intramolecular [3+2] Annulations To Generate Fused Ring Systems
por: Lee, Sarah Yunmi, et al.
Publicado: (2015)

2-Aminobenzaldehydes as Versatile Substrates for Rhodium-Catalyzed Alkyne Hydroacylation: Application to Dihydroquinolone Synthesis**
por: Castaing, Matthias, et al.
Publicado: (2013)

Enantioselective α-functionalizations of ketones via allylic substitution of silyl enol ethers
por: He, Zhi-Tao, et al.
Publicado: (2018)

Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres
por: Nairoukh, Zackaria, et al.
Publicado: (2017)

A Review on Generation and Reactivity of the N-Heterocyclic Carbene-Bound Alkynyl Acyl Azolium Intermediates
por: Dong, Ziyang, et al.
Publicado: (2022)

Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles
por: Wang, Haiyang, et al.
Publicado: (2020)

(S)-2-(1-Hydroxyethyl)benzimidazolium dihydrogen phosphate
por: Xia, Rong
Publicado: (2009)

Crystal Engineering of Ionic Cocrystals Sustained by Azolium···Azole Heterosynthons
por: Rahmani, Maryam, et al.
Publicado: (2022)

N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate
por: Chen, Xiang-Yu, et al.
Publicado: (2017)

Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes
por: Zhao, Changgui, et al.
Publicado: (2018)

Enantioselective, convergent synthesis of the ineleganolide core by a tandem annulation cascade
por: Craig, II, Robert A., et al.
Publicado: (2017)

N-Heterocyclic carbene-catalyzed enantioselective hetero-[10 + 2] annulation
por: Peng, Qiupeng, et al.
Publicado: (2020)

Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C–H Functionalization and Spiroannulation
por: Reddy Chidipudi, Suresh, et al.
Publicado: (2015)

Iridium-Catalyzed Enantioselective Alkene Hydroalkylation via a Heteroaryl-Directed Enolization–Decarboxylation Sequence
por: Jing, Changcheng, et al.
Publicado: (2023)

Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N‐Acyliminium Ions
por: Grossmann, Oleg, et al.
Publicado: (2022)

Enantioselective one-carbon expansion of aromatic rings by simultaneous formation and chromoselective irradiation of a transient coloured enolate
por: Saunthwal, Rakesh K., et al.
Publicado: (2022)

Enantioselective synthesis of planar chiral ferrocenes via palladium-catalyzed annulation with diarylethynes
por: Shi, Yan-Chao, et al.
Publicado: (2013)

Correction: Enantioselective, convergent synthesis of the ineleganolide core by a tandem annulation cascade
por: Craig, Robert A., et al.
Publicado: (2019)

Diastereodivergent and Enantioselective [4+2] Annulations of γ-Butenolides with Cyclic 1-Azadienes
por: Li, Chao, et al.
Publicado: (2015)

Enantioselective hydrogenation of annulated arenes: controlled formation of multiple stereocenters in adjacent rings
por: Wiesenfeldt, Mario P., et al.
Publicado: (2021)

Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol Isomerization
por: Wang, Xiao-Lin, et al.
Publicado: (2022)

Combining silver- and organocatalysis: an enantioselective sequential catalytic approach towards pyrano-annulated pyrazoles
por: Hack, Daniel, et al.
Publicado: (2015)

N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals
por: Ni, Qijian, et al.
Publicado: (2015)

Enantioselective annulation of enals with 2-naphthols by triazolium salts derived from l-phenylalanine
por: Li, Guo-Tai, et al.
Publicado: (2015)

Modular Isoquinoline Synthesis Using Catalytic Enolate Arylation and in Situ Functionalization
por: Pilgrim, Ben S., et al.
Publicado: (2013)

Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3‐Isothiocyanato Oxindoles with Dibenzylidene Ketones
por: Du, Dan, et al.
Publicado: (2016)

Palladium-catalyzed enantioselective decarboxylative allylic alkylation of fully substituted N-acyl indole-derived enol carbonates
por: Alexy, Eric J., et al.
Publicado: (2019)

The Silicon–Hydrogen Exchange Reaction: A Catalytic σ-Bond Metathesis Approach to the Enantioselective Synthesis of Enol Silanes
por: Zhou, Hui, et al.
Publicado: (2020)

Catalytic enantioselective synthesis of 1,4-dihydropyridines via the addition of C(1)-ammonium enolates to pyridinium salts
por: McLaughlin, Calum, et al.
Publicado: (2021)

A Desilylative Approach to Alkyl Substituted C(1)‐Ammonium Enolates: Application in Enantioselective [2+2] Cycloadditions
por: Wang, Yihong, et al.
Publicado: (2022)

Diastereo‐ and Enantioselective Inverse‐Electron‐Demand Diels–Alder Cycloaddition between 2‐Pyrones and Acyclic Enol Ethers
por: Huang, Guanghao, et al.
Publicado: (2022)

Detrifluoroacetylative in Situ Generated Cyclic Fluorinated Enolates for the Preparation of Compounds Featuring a C–F Stereogenic Center
por: Liu, Jiang, et al.
Publicado: (2019)

Mechanochemical generation of acid-degradable poly(enol ether)s
por: Yang, Jinghui, et al.
Publicado: (2021)

Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid
por: Yao, Weijun, et al.
Publicado: (2017)

Cannot write session to /tmp/vufind_sessions/sess_lr4i5t6n934g6majb35ss5ejqm