Cargando…

Vicinal stereocenters via asymmetric allylic alkylation and Cope rearrangement: a straightforward route to functionally and stereochemically rich heterocycles

An asymmetric allylic alkylation/Cope rearrangement (AAA/[3,3]) capable of stereoselectively constructing vicinal stereocenters has been developed. Strategically integrated 4-methylation on the 3,3-dicyano-1,5-diene controls stereoselectivity and drives Cope rearrangement equilibrium in the forward...

Descripción completa

Detalles Bibliográficos
Autores principales:	Nilova, Aleksandra, Mannchen, Michael D., Noel, Abdias N., Semenova, Evgeniya, Grenning, Alexander J.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	The Royal Society of Chemistry 2023
Materias:	Chemistry
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9993902/ https://www.ncbi.nlm.nih.gov/pubmed/36908968 http://dx.doi.org/10.1039/d2sc07021a

Ejemplares similares

Construction of vicinal 4°/3°-carbons via reductive Cope rearrangement
por: Sobie, Kristin M., et al.
Publicado: (2022)

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

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

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

Palladium-catalyzed asymmetric allylic alkylation (AAA) with alkyl sulfones as nucleophiles
por: Trost, Barry M., et al.
Publicado: (2021)

Introducing a sulfone-embedded anhydride to the anhydride-imine reaction for the modular synthesis of N-heterocyclic sulfones bearing vicinal stereocenters
por: Beng, Timothy K., et al.
Publicado: (2023)

A straightforward and convenient synthesis of functionalized allyl thiosulfonates and allyl disulfanes
por: Reddy, Raju Jannapu, et al.
Publicado: (2018)

The Pd-catalysed asymmetric allylic alkylation reactions of sulfamidate imines
por: Pham, Quoc Hoang, et al.
Publicado: (2021)

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

Pd-catalyzed asymmetric allylic alkylations via C–H activation of N-allyl imines with glycinates
por: Trost, Barry M., et al.
Publicado: (2017)

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

Radical asymmetric intramolecular α-cyclopropanation of aldehydes towards bicyclo[3.1.0]hexanes containing vicinal all-carbon quaternary stereocenters
por: Ye, Liu, et al.
Publicado: (2018)

Copper-catalyzed asymmetric allylic alkylation of racemic inert cyclic allylic ethers under batch and flow conditions
por: Li, Jun, et al.
Publicado: (2023)

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)

Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Thietane 1,1-Dioxides
por: Laidlaw, Gillian, et al.
Publicado: (2021)

Stereodivergent synthesis via iridium-catalyzed asymmetric double allylic alkylation of cyanoacetate
por: Shen, Chong, et al.
Publicado: (2021)

The Stereochemical Course of the α-Hydroxyphosphonate–Phosphate Rearrangement
por: Pallitsch, Katharina, et al.
Publicado: (2015)

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

Asymmetric Synthesis of α-Allyl-α-Aryl α-Amino Acids by Tandem Alkylation/π-Allylation of α-Iminoesters
por: Curto, John M., et al.
Publicado: (2014)

Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade
por: Šiaučiulis, Mindaugas, et al.
Publicado: (2017)

Asymmetric Suzuki-Miyaura coupling of heterocycles via Rhodium-catalysed allylic arylation of racemates
por: Schäfer, Philipp, et al.
Publicado: (2017)

Recent Advances in the Application of Chiral Phosphine Ligands in Pd-Catalysed Asymmetric Allylic Alkylation
por: Rios, Itzel Guerrero, et al.
Publicado: (2011)

Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems
por: Augustin, André U., et al.
Publicado: (2022)

Catalytic Enantioselective Synthesis of Heterocyclic Vicinal Fluoroamines by Using Asymmetric Protonation: Method Development and Mechanistic Study
por: Ashford, Matthew W., et al.
Publicado: (2020)

The Allylic Alkylation of Ketone Enolates
por: Junk, Lukas, et al.
Publicado: (2020)

Catalytic Asymmetric Synthesis of Tröger’s Base Analogues with Nitrogen Stereocenter
por: Ma, Chun, et al.
Publicado: (2023)

Doubly stereoconvergent construction of vicinal all-carbon quaternary and tertiary stereocenters by Cu/Mg-catalyzed propargylic substitution
por: Pu, Xiang, et al.
Publicado: (2022)

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)

Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters
por: Yan, Lin, et al.
Publicado: (2013)

Enantioselective synthesis of gem-disubstituted N-Boc diazaheterocycles via decarboxylative asymmetric allylic alkylation
por: Sun, Alexander W., et al.
Publicado: (2018)

Effective synthesis of bicyclodienes via palladium-catalyzed asymmetric allylic alkylation and ruthenium-catalyzed cycloisomerization
por: HAVARE, Nizam
Publicado: (2020)

Influence of Achiral Phosphine Ligands on a Synergistic Organo‐ and Palladium‐Catalyzed Asymmetric Allylic Alkylation
por: McLeod, David, et al.
Publicado: (2022)

Author Correction: Asymmetric Suzuki-Miyaura coupling of heterocycles via Rhodium-catalysed allylic arylation of racemates
por: Schäfer, Philipp, et al.
Publicado: (2018)

Spiro-fused carbohydrate oxazoline ligands: Synthesis and application as enantio-discrimination agents in asymmetric allylic alkylation
por: Kraft, Jochen, et al.
Publicado: (2016)

Copper-catalysed asymmetric allylic alkylation of alkylzirconocenes to racemic 3,6-dihydro-2H-pyrans
por: Rideau, Emeline, et al.
Publicado: (2015)

Development of an Enantioselective Allylic Alkylation of Acyclic α‐Fluoro‐β‐ketoesters for Asymmetric Synthesis of 3‐Fluoropiperidines
por: Han, Jiaxin, et al.
Publicado: (2022)

Stereocontrolled synthesis of some novel functionalized heterocyclic amino ester and amide derivatives with multiple stereocenters
por: Semghouli, Anas, et al.
Publicado: (2023)

Stereospecific Asymmetric Synthesis of Tertiary Allylic Alcohol Derivatives by Catalytic [2,3]‐Meisenheimer Rearrangements
por: Yu, Xin, et al.
Publicado: (2020)

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

Cannot write session to /tmp/vufind_sessions/sess_log1jjo8lijssrvibdg3352gce