Cargando…

Asymmetric addition of Grignard reagents to ketones: culmination of the ligand-mediated methodology allows modular construction of chiral tertiary alcohols

A new class of biaryl chiral ligands derived from 1,2-diaminocyclohexane (1,2-DACH) has been designed to enable the asymmetric addition of aliphatic and, for the first time, aromatic Grignard reagents to ketones for the preparation of highly enantioenriched tertiary alcohols (up to 95% ee). The newl...

Descripción completa

Detalles Bibliográficos
Autores principales:	Monasterolo, Claudio, O'Gara, Ryan, Kavanagh, Saranna E., Byrne, Sadbh E., Bieszczad, Bartosz, Murray, Orla, Wiesinger, Michael, Lynch, Rebecca A., Nikitin, Kirill, Gilheany, Declan G.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	The Royal Society of Chemistry 2022
Materias:	Chemistry
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9159101/ https://www.ncbi.nlm.nih.gov/pubmed/35733895 http://dx.doi.org/10.1039/d1sc06350b

Ejemplares similares

Very short highly enantioselective Grignard synthesis of 2,2-disubstituted tetrahydrofurans and tetrahydropyrans
por: Monasterolo, Claudio, et al.
Publicado: (2019)

Copper-Free Alternatives to Access Ketone Building Blocks from Grignard Reagents
por: Taeschler, Christoph, et al.
Publicado: (2022)

Pd-catalyzed allylative dearomatisation using Grignard reagents
por: Boldrini, Cosimo, et al.
Publicado: (2021)

Grignard Reagent-Catalyzed Hydroboration of Esters, Nitriles, and Imines
por: Han, Hyun Ji, et al.
Publicado: (2023)

Regioselectivity in Reactions between Bis(2-benzothiazolyl)ketone and Vinyl Grignard Reagents: C- versus O-alkylation—Part III †
por: Boga, Carla, et al.
Publicado: (2018)

Catalytic enantioselective addition of Grignard reagents to aromatic silyl ketimines
por: Rong, Jiawei, et al.
Publicado: (2016)

Investigation of Grignard Reagent as an Advanced Base for Aza-Claisen Rearrangement
por: Song, Bo Reum, et al.
Publicado: (2019)

Synthesis of Bis-heteroaryls Using Grignard Reagents and Pyridylsulfonium Salts
por: Horan, Alexandra M., et al.
Publicado: (2021)

Halogenation Reactions of Alkyl Alcohols Employing Methyl Grignard Reagents
por: Hirbawi, Nadia, et al.
Publicado: (2022)

Continuous flow synthesis of diaryl ketones by coupling of aryl Grignard reagents with acyl chlorides under mild conditions in the ecofriendly solvent 2-methyltetrahydrofuran
por: Zhang, Chuan-Tao, et al.
Publicado: (2019)

Transition metal-free domino acyl substitution/Michael addition of alkenyl Grignard reagents to lactam esters: synthesis of lactam-bearing homoallylic ketones
por: Farah, Abdikani Omar, et al.
Publicado: (2020)

Tertiary amine synthesis via reductive coupling of amides with Grignard reagents
por: Xie, Lan-Gui, et al.
Publicado: (2017)

Cobalt-Catalyzed (Hetero)arylation of Saturated Cyclic Amines with Grignard Reagents
por: Barré, Baptiste, et al.
Publicado: (2018)

Unusual Nucleophilic Addition of Grignard Reagents in the Synthesis of 4-Amino-pyrimidines
por: Tinson, Ryan A. J., et al.
Publicado: (2018)

Highly Enantioselective Catalytic Addition of Grignard Reagents to N‐Heterocyclic Acceptors
por: Guo, Yafei, et al.
Publicado: (2019)

Enantioselective Catalytic Dearomative Addition of Grignard Reagents to 4-Methoxypyridinium Ions
por: Guo, Yafei, et al.
Publicado: (2021)

Morphological Plasticity of LiCl Clusters Interacting with Grignard Reagent in Tetrahydrofuran
por: de Giovanetti, Marinella, et al.
Publicado: (2023)

Copper-Catalyzed Oxidative Homo- and Cross-Coupling of Grignard Reagents Using Diaziridinone
por: Zhu, Yingguang, et al.
Publicado: (2014)

Kumada–Tamao–Corriu Type Reaction of Aromatic Bromo- and Iodoamines with Grignard Reagents
por: Zielińska, Alicja A., et al.
Publicado: (2023)

Iron‐catalyzed Cross‐Coupling of Propargyl Carboxylates and Grignard Reagents: Synthesis of Substituted Allenes
por: Kessler, Simon N., et al.
Publicado: (2016)

Copper‐Catalyzed Addition of Grignard Reagents to in situ Generated Indole‐Derived Vinylogous Imines
por: Ge, Luo, et al.
Publicado: (2020)

Fe-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and Grignard reagents
por: Liu, Lei, et al.
Publicado: (2020)

Iron-Catalyzed Coupling of Aryl Grignard Reagents with Alkyl Halides: A Competitive Hammett Study**
por: Hedström, Anna, et al.
Publicado: (2011)

Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Benzylic Ethers with Isotopically-Labeled Grignard Reagents
por: Dawson, David D., et al.
Publicado: (2015)

Iron‐Catalyzed Cross‐Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow
por: Deng, Yuchao, et al.
Publicado: (2019)

Iron‐Catalyzed Cross‐Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols
por: Posevins, Daniels, et al.
Publicado: (2021)

Sequential olefination–dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard or zinc reagent
por: Yu, Lei, et al.
Publicado: (2022)

Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo‐Organomagnesium Anilides
por: Colas, Kilian, et al.
Publicado: (2022)

Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex
por: Hashimoto, Toru, et al.
Publicado: (2019)

Stereocontrolled addition of Grignard reagents to oxa-bridged benzazepines: highly efficient synthesis of functionalized benzazepine scaffolds
por: Zhang, Yuewei, et al.
Publicado: (2020)

Iron-Catalyzed Cross-Coupling of α-Allenyl Esters with Grignard Reagents for the Synthesis of 1,3-Dienes
por: Kong, Wei-Jun, et al.
Publicado: (2023)

A Synthesis of Substituted α-Allenols via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard Reagents
por: Kessler, Simon N., et al.
Publicado: (2016)

Culmination of Low-Dose Pesticide Effects
por: Liess, Matthias, et al.
Publicado: (2013)

Presentation of research in anesthesia: Culmination into publication?
por: Tyagi, Asha, et al.
Publicado: (2013)

C−N Axial Chiral Hypervalent Iodine Reagents: Catalytic Stereoselective α‐Oxytosylation of Ketones
por: Alharbi, Haifa, et al.
Publicado: (2021)

Iron-Catalyzed C(sp(2))–C(sp(3)) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents
por: Bisz, Elwira, et al.
Publicado: (2020)

Regioselective addition of Grignard reagents to N-acylpyrazinium salts: synthesis of substituted 1,2-dihydropyrazines and Δ(5)-2-oxopiperazines
por: St. Hilaire, Valentine R, et al.
Publicado: (2019)

Cardiac Sarcoidosis Culminating in Severe Biventricular Failure
por: Ozaki, Takefumi, et al.
Publicado: (2009)

Apicoectomy—The Culmination of Perfect Root-Canal Operations
por: Gross, S. Sidney
Publicado: (1920)

Conjugate Addition of Grignard Reagents to Thiochromones Catalyzed by Copper Salts: A Unified Approach to Both 2-Alkylthiochroman-4-One and Thioflavanone
por: Bellinger, Tania J., et al.
Publicado: (2020)

Cannot write session to /tmp/vufind_sessions/sess_k5isdkglbltnrts606q39jkudv