Cargando…

Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols

The first nickel-catalyzed enantioselective allylic alkylation of lactone and lactam substrates to deliver products bearing an all-carbon quaternary stereocenter is reported. The reaction, which utilizes a commercially available chiral bisphosphine ligand, proceeds in good yield with a high level of...

Descripción completa

Detalles Bibliográficos
Autores principales:	Ngamnithiporn, Aurapat, Jette, Carina I., Bachman, Shoshana, Virgil, Scott C., Stoltz, Brian M.
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/PMC5912103/ https://www.ncbi.nlm.nih.gov/pubmed/29732133 http://dx.doi.org/10.1039/c7sc05216b

Ejemplares similares

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)

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

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

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

Tandem Dearomatization/Enantioselective Allylic Alkylation of Pyridines
por: Greßies, Steffen, et al.
Publicado: (2023)

Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes
por: Lin, Zhiyang, et al.
Publicado: (2021)

Iridium-catalyzed enantioselective alkynylation and kinetic resolution of alkyl allylic alcohols
por: Guo, Jia, et al.
Publicado: (2022)

Iridium-catalyzed enantioselective direct vinylogous allylic alkylation of coumarins
por: Sarkar, Rahul, et al.
Publicado: (2018)

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

Copper-Catalyzed Enantioselective Borylative Allyl–Allyl Coupling of Allenes and Allylic gem-Dichlorides
por: Piñeiro-Suárez, Martín, et al.
Publicado: (2023)

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

Mechanistic insights into rhodium-catalyzed enantioselective allylic alkylation for quaternary stereogenic centers
por: Pareek, Monika, et al.
Publicado: (2020)

Iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation
por: Sarkar, Rahul, et al.
Publicado: (2021)

Correction: Iridium-catalyzed enantioselective olefinic C(sp(2))–H allylic alkylation
por: Sarkar, Rahul, et al.
Publicado: (2021)

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

Development of (Trimethylsilyl)ethyl Ester Protected Enolates and Applications in Palladium-Catalyzed Enantioselective Allylic Alkylation: Intermolecular Cross-Coupling of Functionalized Electrophiles
por: Reeves, Corey M., et al.
Publicado: (2014)

Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes
por: Xu, Guoxing, et al.
Publicado: (2018)

Access to dialkylated allylic stereogenic centers by Ni-catalysed enantioselective hydrovinylation of unactivated alkenes
por: Zhang, Jian-Xin, et al.
Publicado: (2022)

Synthesis of 1-[bis(trifluoromethyl)phosphine]-1’-oxazolinylferrocene ligands and their application in regio- and enantioselective Pd-catalyzed allylic alkylation of monosubstituted allyl substrates
por: Lai, Zeng-Wei, et al.
Publicado: (2014)

Spiro Indane-Based Phosphine-Oxazolines as Highly Efficient P,N Ligands for Enantioselective Pd-Catalyzed Allylic Alkylation of Indoles and Allylic Etherification
por: Qiu, Zhongxuan, et al.
Publicado: (2019)

Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles
por: Zhang, Xiao, et al.
Publicado: (2015)

Nickel-catalyzed allylic carbonylative coupling of alkyl zinc reagents with tert-butyl isocyanide
por: Weng, Yangyang, et al.
Publicado: (2020)

Bi(III)-Catalyzed Enantioselective Allylation Reactions of Ketimines
por: Wang, Jie, et al.
Publicado: (2019)

Boron-Catalyzed, Diastereo- and Enantioselective Allylation of Ketones with Allenes
por: Nicholson, Kieran, et al.
Publicado: (2022)

Enantioselective Csp3-Csp3 formation by nickel-catalyzed enantioconvergent cross-electrophile alkyl-alkyl coupling of unactivated alkyl halides
por: Zhao, Wen-Tao, et al.
Publicado: (2023)

Enantioselective Nickel‐Catalyzed Intramolecular Allylic Alkenylations Enabled by Reversible Alkenylnickel E/Z Isomerization
por: Yap, Connor, et al.
Publicado: (2017)

Enantioselective nickel-catalyzed arylative and alkenylative intramolecular 1,2-allylations of tethered allene–ketones
por: Di Sanza, Riccardo, et al.
Publicado: (2020)

Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines
por: Grange, Rebecca L., et al.
Publicado: (2015)

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

Highly Enantioselective Hiyama Cross-Coupling via Rh-Catalyzed Allylic Arylation of Racemic Allyl Chlorides
por: González, Jesús, et al.
Publicado: (2019)

Enantioselective Nozaki–Hiyama–Kishi allylation-lactonization for the syntheses of 3-substituted phthalides
por: Kumbhar, Sharad V., et al.
Publicado: (2018)

Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols
por: Yang, Guo-Hui, et al.
Publicado: (2019)

Nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters
por: Lu, Xi, et al.
Publicado: (2018)

Palladium-Catalyzed Cascade Wacker/Allylation Sequence with Allylic Alcohols Leading to Allylated Dihydropyrones
por: Huang, Wen-Yu, et al.
Publicado: (2017)

Copper-Catalyzed Oxidative Dehydrogenative Carboxylation of Unactivated Alkanes to Allylic Esters via Alkenes
por: Tran, Ba L., et al.
Publicado: (2014)

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

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation
por: Rossi‐Ashton, James A., et al.
Publicado: (2020)

Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides
por: Fang, Yi, 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)

Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols
por: Estopiñá-Durán, Susana, et al.
Publicado: (2020)

Cannot write session to /tmp/vufind_sessions/sess_v5ecgv3c6dpa89o1d295d8ti7o