Palladium(0)-catalyzed rearrangement of allyl enol ethers to form chiral quaternary carbon centers via asymmetric allylic alkylation
Sign Up to like & getrecommendations! Published in 2018 at "Tetrahedron Letters"
DOI: 10.1016/j.tetlet.2018.07.065
Abstract: Abstract Herein we report the first palladium(0)-catalyzed asymmetric allylic alkylation (AAA) of allyl enol ether via π -allylpalladium intermediate using Trost chiral diphosphine. This unprecedented reaction produced very rare α-aryl quaternary aldehydes with multi-functional groups.… read more here.
Keywords: enol ethers; allylic alkylation; asymmetric allylic; palladium catalyzed ... See more keywords
Palladium-Catalyzed Asymmetric Allylic C-H Functionalization: Mechanism, Stereo- and Regioselectivities, and Synthetic Applications.
Sign Up to like & getrecommendations! Published in 2020 at "Accounts of chemical research"
DOI: 10.1021/acs.accounts.0c00477
Abstract: ConspectusAsymmetric functionalization of inert C-H bonds is undoubtedly a synthetically significant yet challenging bond-forming process, allowing for the preparation of densely functionalized molecules from abundantly available feedstocks. In the past decade, our group and others… read more here.
Keywords: functionalization; catalyzed asymmetric; allylic alkylation; asymmetric allylic ... See more keywords
Iridium-Catalyzed Asymmetric Allylic Alkylation of Deconjugated Butyrolactams.
Sign Up to like & getrecommendations! Published in 2021 at "Organic letters"
DOI: 10.1021/acs.orglett.1c00697
Abstract: Compared with the ever-growing list of nonprochiral nucleophiles in Ir-catalyzed asymmetric allylic substitution reactions, prochiral nucleophiles are less studied. We present a new prochiral nucleophile, namely, deconjugated butyrolactam, for Ir-catalyzed asymmetric allylic alkylation (AAA). This… read more here.
Keywords: catalyzed asymmetric; allylic alkylation; asymmetric allylic; iridium catalyzed ... See more keywords
Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Thietane 1,1-Dioxides.
Sign Up to like & getrecommendations! Published in 2021 at "Organic letters"
DOI: 10.1021/acs.orglett.1c04075
Abstract: A palladium-catalyzed decarboxylative asymmetric allylic alkylation of thietane 1,1-dioxides via linear enolate intermediates from racemic starting materials has been developed. This process installs an α-sulfonyl tetrasubstituted stereogenic center with high enantioselectivity. The potential to transform… read more here.
Keywords: decarboxylative asymmetric; catalyzed decarboxylative; alkylation thietane; asymmetric allylic ... See more keywords
Pd-Catalyzed Asymmetric Allylic Substitution Cascade of Substituted 4-Hydroxy-2H-pyrones with meso-Allyl Dicarbonates.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00937
Abstract: An efficient Pd-catalyzed asymmetric allylic substitution cascade of 4-hydroxy-2H-pyrones with meso-allyl dicarbonates has been developed for the synthesis of kinetic chiral tetrahydro-1H-pyrano[4,3-b]benzofuran-1-one products in ≤87% yield and ≤99% ee. The protocol was achieved via a… read more here.
Keywords: allylic substitution; pyrones meso; substitution cascade; catalyzed asymmetric ... See more keywords
Chiral Brønsted Acid-Catalyzed Intramolecular Asymmetric Allylic Alkylation of Indoles with Primary Alcohols.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01253
Abstract: Herein, chiral Brønsted acid-catalyzed intramolecular asymmetric allylic alkylation of indoles with allylic primary alcohols is described. The allyl alcohols were directly employed as the allylic precursors in this metal-free protocol, without preactivation or any additional… read more here.
Keywords: intramolecular asymmetric; catalyzed intramolecular; chiral nsted; nsted acid ... See more keywords
Catalytic Asymmetric Allylic Substitution/Isomerization with Central Chirality Transposition.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01559
Abstract: We have developed a catalytic asymmetric allylic substitution/isomerization process with central chirality transposition. This process takes advantage of the ambident reactivity of the 2-indole imine methide generated in situ from racemic tertiary indolylmethanols. The use… read more here.
Keywords: allylic substitution; chirality transposition; central chirality; substitution isomerization ... See more keywords
Route to Chiral Tetrahydrofuran Acetals via Pd-Catalyzed Asymmetric Allylic Cycloaddition of Vinyl Epoxides with β-Keto Enol Ethers.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02437
Abstract: An efficient method for the synthesis of functionalized chiral tetrahydrofuran (THF) acetals via Pd-catalyzed asymmetric allylic cycloaddition has been developed. With a palladium catalyst coordinated by a chiral phosphine ligand, the protocol is enabled to… read more here.
Keywords: allylic cycloaddition; via catalyzed; acetals via; catalyzed asymmetric ... See more keywords
Palladium(0)-Catalyzed Intermolecular Asymmetric Allylic Dearomatization of Substituted β-Naphthols with Morita-Baylis-Hillman (MBH) Adducts.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c03262
Abstract: Pd-catalyzed intermolecular asymmetric allylic dearomatization of substituted β-naphthol derivatives with Boc-protected Morita-Baylis-Hillman (MBH) adducts was developed. The reaction occurs smoothly in 1,4-dioxane at room temperature in the presence of [Pd(C3H5)Cl]2 (2.5 mol %), (S, Sp)-PHOX… read more here.
Keywords: morita baylis; allylic dearomatization; intermolecular asymmetric; catalyzed intermolecular ... See more keywords
Asymmetric Allylic Alkylation of β-Ketoesters via C–N Bond Cleavage of N-Allyl-N-methylaniline Derivatives Catalyzed by a Nickel–Diphosphine System
Sign Up to like & getrecommendations! Published in 2020 at "ACS Catalysis"
DOI: 10.1021/acscatal.0c01356
Abstract: Nickel complexes bearing chiral diphosphine ligands, such as (S)-Tol-MeO-BIPHEP and (S)-H8-BINAP, serve as efficient catalysts for asymmetric allylic alkylation (AAA) of β-ketoesters, using allylic... read more here.
Keywords: allylic alkylation; alkylation ketoesters; asymmetric allylic; via bond ... See more keywords
A Pd-catalyzed asymmetric allylic substitution cascade via an asymmetric desymmetrization for the synthesis of bicyclic dihydrofurans.
Sign Up to like & getrecommendations! Published in 2019 at "Chemical communications"
DOI: 10.1039/c9cc07204g
Abstract: A Pd-catalyzed asymmetric allylic substitution cascade of allylic meso-dicarbonates with 3-oxo-nitriles has been developed for the synthesis of chiral bicyclic dihydrofurans bearing two vicinal carbon stereocenters. The reaction proceeds via an asymmetric desymmetrization process with… read more here.
Keywords: catalyzed asymmetric; asymmetric allylic; bicyclic dihydrofurans; allylic substitution ... See more keywords