Enantioconvergent alkylation of ketones with racemic secondary alcohols via hydrogen borrowing catalysis

Enantioconvergent alkylation of ketones with racemic secondary alcohols via hydrogen borrowing catalysis

An enantioconvergent method for the alkylation of o-disubstituted aryl ketones with racemic secondary alcohols is described. This process is mediated by a commercially available iridium catalyst and proceeds via hydrogen borrowing catalysis. The highly enantioenriched β-substituted ketone products w...

Descripció completa

Dades bibliogràfiques
Autors principals:	Cheang, DMJ, Armstrong, RJ, Akhtar, WM, Donohoe, TJ
Format:	Journal article
Idioma:	English
Publicat:	Royal Society of Chemistry 2020

Ítems similars

The α-alkylation of ketones using hydrogen borrowing catalysis
per: Akhtar, W
Publicat: (2018)

Stereoselective synthesis of alicyclic ketones: a hydrogen borrowing approach
per: Armstrong, RJ, et al.
Publicat: (2019)

Controlling absolute stereochemistry in hydrogen borrowing catalysed alkylation
per: Cheang, DMJ-Y
Publicat: (2023)

Enantioconvergent catalysis
per: Justin T. Mohr, et al.
Publicat: (2016-09-01)

Dynamic kinetic resolution allows control of remote stereochemistry in asymmetric hydrogen borrowing alkylation
per: Cheang, DMJ, et al.
Publicat: (2025)

Hydrogen borrowing catalysis using 1° and 2° alcohols: investigation and scope leading to α and β branched products
per: Frost, JR, et al.
Publicat: (2021)

Strategic application and transformation of ortho-disubstituted phenyl and cyclopropyl ketones to expand the scope of hydrogen borrowing catalysis.
per: Frost, J, et al.
Publicat: (2015)

Functional group tolerant hydrogen borrowing C-alkylation
per: Bailey, EP, et al.
Publicat: (2024)

Functional group tolerant hydrogen borrowing C-alkylation
per: Bailey, EP, et al.
Publicat: (2024)

Enantioconvergent Cross-Couplings of Racemic Alkylmetal Reagents with Unactivated Secondary Alkyl Electrophiles: Catalytic Asymmetric Negishi α-Alkylations of N-Boc-Pyrrolidine
per: Cordier, Christopher J., et al.
Publicat: (2018)

The iridium-catalysed alkylation of aromatic ketones via hydrogen borrowing
per: Cheong, C
Publicat: (2018)

Hydrogen borrowing catalysis with secondary alcohols: a new route for the generation of β-branched carbonyl compounds
per: Akhtar, W, et al.
Publicat: (2017)

Hydrogen-Borrowing and Interrupted-Hydrogen-Borrowing Reactions of Ketones and Methanol Catalyzed by Iridium.
per: Shen, D, et al.
Publicat: (2014)

Hydrogen-borrowing and interrupted-hydrogen-borrowing reactions of ketones and methanol catalyzed by iridium
per: Shen, D, et al.
Publicat: (2015)

Iridium-catalyzed C4-alkylation of 2,6-di-tert-butylphenol by using hydrogen-borrowing catalysis
per: Frost, J, et al.
Publicat: (2016)

Heterogeneous Mn@CeO2 Catalyst for α‑Alkylation of Ketones with Alcohols via Hydrogen-Borrowing Strategy
per: Rajagopal Swaathy, et al.
Publicat: (2025-02-01)

Extension of hydrogen borrowing alkylation reactions for the total synthesis of (–)-γ-lycorane
per: Hall, C, et al.
Publicat: (2022)

Control of absolute stereochemistry in transition-metal-catalyzed hydrogen borrowing reactions
per: Kwok, T, et al.
Publicat: (2020)

Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids
per: Hall, CJJ, et al.
Publicat: (2021)

Functional group tolerant hydrogen borrowing C-alkylation
per: Elliot P. Bailey, et al.
Publicat: (2024-06-01)

Ni-catalyzed enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohols and aryl bromides
per: Li-Li Zhang, et al.
Publicat: (2024-03-01)

Ligand‐Promoted [Pd]‐Catalyzed α‐Alkylation of Ketones through a Borrowing‐Hydrogen Approach
per: Dr. Seetharaman Manojveer, et al.
Publicat: (2023-01-01)

Enantioconvergent nucleophilic substitution via synergistic phase-transfer catalysis
per: Dooley, C, et al.
Publicat: (2025)

Ligand-enabled Ni-catalysed enantioconvergent intermolecular Alkyl-Alkyl cross-coupling between distinct Alkyl halides
per: Wen-Tao Zhao, et al.
Publicat: (2023-05-01)

Enantioconvergent construction of stereogenic silicon via Lewis base-catalyzed dynamic kinetic silyletherification of racemic chlorosilanes
per: Tianbao Hu, et al.
Publicat: (2023-08-01)

Catalytic asymmetric synthesis of cyclohexanes by hydrogen borrowing annulations
per: Armstrong, R, et al.
Publicat: (2019)

Formal enantioconvergent substitution of alkyl halides via catalytic asymmetric photoredox radical coupling
per: Jiangtao Li, et al.
Publicat: (2018-06-01)

Enantioconvergent halogenophilic nucleophilic substitution (SN2X) reaction by chiral phase-transfer catalysis
per: Zhang, Xin
Publicat: (2019)

Cyclometalated Iridium Complex-Catalyzed N‑Alkylation of Amines with Alcohols via Borrowing Hydrogen in Aqueous Media
per: NianHua Luo, et al.
Publicat: (2020-10-01)

Pentamethylphenyl (Ph*) ketones: Unique building blocks for organic synthesis
per: Armstrong, R, et al.
Publicat: (2021)

Asymmetric Alkyl−Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins
per: Owston, Nathan A., et al.
Publicat: (2013)

Recent developments in transition metal-catalyzed asymmetric borrowing hydrogen catalysis
per: Nidhi Garg, et al.
Publicat: (2023-12-01)

A vinyl cyclopropane ring expansion and iridium‐catalyzed hydrogen borrowing cascade
per: Wübbolt, S, et al.
Publicat: (2020)

A vinyl cyclopropane ring expansion and iridium‐catalyzed hydrogen borrowing cascade
per: Wubbolt, S, et al.
Publicat: (2020)

The Allylic Alkylation of Ketone Enolates
per: Dr. Lukas Junk, et al.
Publicat: (2020-09-01)

Hydrogen borrowing-based methods for the construction of quaternary stereocentres
per: Crompton, J, et al.
Publicat: (2025)

Development of functional group tolerant and room temperature hydrogen borrowing enolate alkylation reactions
per: Bailey, EP
Publicat: (2023)

Asymmetric α-C(sp 3)−H allylic alkylation of primary alkylamines by synergistic Ir/ketone catalysis
per: Jianyu Li, et al.
Publicat: (2024-01-01)

Parallel kinetic resolution of racemic ketones through reduction: a quantitative analysis
per: Juan R. Dehli, et al.
Publicat: (2002-06-01)

Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic α-Chloroamides
per: Lundin, Pamela M., et al.
Publicat: (2013)