Organic Letters, Год журнала: 2024, Номер 26(27), С. 5646 - 5651
Опубликована: Июль 2, 2024
The development of site-selective and regio- enantioselective reactions substrates with multiple active sites is an important topic remains a substantial challenge in synthetic chemistry. Here, we describe rhodium-catalyzed asymmetric
Язык: Английский
Organic Letters, Год журнала: 2023, Номер 25(10), С. 1722 - 1726
Опубликована: Март 4, 2023
Direct N-allylation of azoles with hydrogen evolution has been achieved through the synergistic combination organic photocatalysis and cobalt catalysis. The protocol bypasses stoichiometric oxidants prefunctionalization alkenes produces (H2) as byproduct. This transformation highlights high step- atom-economy, efficiency, broad functional group tolerance for further derivatization, which opens a door C-N bond formation that is valuable in heterocyclic chemistry.
Язык: Английский
Процитировано
21
Angewandte Chemie International Edition, Год журнала: 2025, Номер unknown
Опубликована: Март 7, 2025
Enantioenriched α-aminoketones serve as important substructures in life science and precursors for the synthesis of diverse value-added targets organic biochemistry. However, direct access to enantioenriched from simple readily available starting materials remains a formidable challenge. Herein, we report an unprecedented nickel-catalyzed asymmetric cross-coupling protocol α-N-heteroaryl ketones alkenes enamines presence carbon monoxide surrogate. The success this reaction relies on sorting two different along with control regio- enantioselectivity. This reductive-oxidative carbonylation unactivated featuring use surrogate allows gas-free streamlined assembly distinct alkenes.
Язык: Английский
Процитировано
1
Angewandte Chemie, Год журнала: 2019, Номер 131(47), С. 17010 - 17014
Опубликована: Сен. 18, 2019
Abstract Photochemical enantioselective nickel‐catalyzed cross‐coupling reactions are difficult to implement. We report a visible‐light‐mediated strategy that successfully couples symmetrical anhydrides and 4‐alkyl dihydropyridines (DHPs) afford enantioenriched α‐substituted ketones under mild conditions. The chemistry does not require exogenous photocatalysts. It is triggered by the direct excitation of DHPs, which act as radical source reductant, facilitating turnover chiral catalytic nickel complex.
Язык: Английский
Процитировано
52
Organic Letters, Год журнала: 2020, Номер 22(9), С. 3519 - 3523
Опубликована: Апрель 17, 2020
Cobalt-catalyzed highly branched- and enantioselective allylic alkylation of malononitriles has been developed. Chiral γ,δ-unsaturated could be synthesized with >20:1 branched/linear regioselectivity up to 99% enantiomeric excess from easily accessible racemic carbonates under mild reaction conditions. The electron-rich sterically less hindered bisoxazolinephosphine ligand is essential realize the high reactivity in carbon–carbon bond formation process.
Язык: Английский
Процитировано
50
Journal of the American Chemical Society, Год журнала: 2020, Номер 142(36), С. 15276 - 15281
Опубликована: Авг. 20, 2020
A highly branch- and enantioselective 1,4-enynes synthesis from readily available terminal alkynes racemic allylic carbonates by Sonogashira type synergistic Rh Cu catalysis under neutral conditions has been developed. Aliphatic aromatic with various functional groups could be used directly. An inner-sphere reductive elimination C(sp)–C(sp3) bond formation mechanism is supported the stoichiometric reaction.
Язык: Английский
Процитировано
47
ACS Catalysis, Год журнала: 2020, Номер 10(8), С. 4491 - 4496
Опубликована: Март 23, 2020
Rhodium(I)/bisoxazolinephosphine combination has been developed as a general catalyst to achieve the dynamic kinetic asymmetric allylation of variety nitrogen, carbon, oxygen, and sulfur pronucleophiles from branched racemic allylic carbonates. Exclusive branch-selectivity up 99% enantiomeric excess could be obtained under neutral conditions. Linear substrates (both Z E) converted same chiral products with excellent regio- enantioselectivities well. Chiral π-allyl-Rh(III)/NPN intermediate was isolated characterized understand origin high selectivities.
Язык: Английский
Процитировано
45
Nature Communications, Год журнала: 2022, Номер 13(1)
Опубликована: Ноя. 11, 2022
Abstract Enantioenriched N -alkylindole compounds, in which nitrogen is bound to a stereogenic sp 3 carbon, are an important entity of target molecules the fields biological, medicinal, and organic chemistry. Despite considerable efforts aimed at inventing methods for stereoselective indole functionalization, straightforward access diverse range chiral -alkylindoles intermolecular catalytic fashion from readily available substrates remains ongoing challenge. In sharp contrast existing C–N bond-forming strategies, here, we describe modular nickel-catalyzed C–C coupling protocol that couples broad array -indolyl-substituted alkenes with aryl/alkenyl/alkynyl bromides produce adducts single regioisomeric form, up 91% yield 97% ee. The process amenable proceed under mild conditions exhibit scope high functional group compatibility. Utility highlighted through late-stage functionalization natural products drug molecules, preparation building blocks.
Язык: Английский
Процитировано
24
Nature Communications, Год журнала: 2020, Номер 11(1)
Опубликована: Янв. 13, 2020
Abstract Catalytic asymmetric functionalization of the N–H groups indoles and carbazoles constitutes an important but less developed class reactions. Herein, we describe a propargylation protocol involving use lithium SPINOL phosphate as chiral catalyst our recently C-alkynyl N,O-acetals propargylating reagents. The direct N-propargylation provides hitherto inaccessible N-functionalized products. Notably, efficiency system allows reactions to be run at very low loading (as 0.1 mol%). Mechanistic information about titled reaction is also disclosed. This study represents advance in bonds carbazoles, additionally expands on application alkali metal salts phosphoric acids catalysis.
Язык: Английский
Процитировано
37
Organic Letters, Год журнала: 2024, Номер 26(18), С. 3966 - 3971
Опубликована: Апрель 26, 2024
Here we report the first example of iridium-catalyzed asymmetric
Язык: Английский
Процитировано
4
Organic Letters, Год журнала: 2019, Номер 21(18), С. 7228 - 7232
Опубликована: Сен. 11, 2019
An unprecedented regio-controllable allylic amination of unactivated dienyl and trienyl alcohols has been developed, providing an efficient approach toward the site-selective formation C1-, C3-, C5-/C7-amination products from sole substrates. Key to this protocol is use secondary amines as reagents, well presence iridium catalyst scandium triflate.
Язык: Английский
Процитировано
27