New Journal of Chemistry, Год журнала: 2024, Номер 48(28), С. 12793 - 12799
Опубликована: Янв. 1, 2024
An I 2 -mediated β-C(sp )–H chalcogenylation of enamides under mild and rapid conditions has been developed. Sequential addition PIFA led to valuable 5-thio- 5-seleno-2-pyridones with a free C3 position.
Язык: Английский
Organic Letters, Год журнала: 2024, Номер 26(11), С. 2321 - 2325
Опубликована: Март 11, 2024
A highly diastereoselective synthesis of spiroisoindolinones from enamides and 3-hydroxy-isoindolinones is reported. The reaction proceeds rapidly in the presence p-toluenesulfonic acid as a Brønsted catalyst affords variety densely substituted with three contiguous stereogenic centers high yields (≤98%) diastereoselectivities (up to dr >98:<2:0:0).
Язык: Английский
Процитировано
3
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4319 - 4325
Опубликована: Март 23, 2024
Earth-abundant-metal catalyzed double bond transposition offers a sustainable and atom-economical route toward the synthesis of internal alkenes. With an emphasis specifically on olefins ethers, isomerization allylic amines has been particularly under represented in literature. Herein, we report efficient methodology for selective N-allylic organic compounds, including amines, amides, imines. The reaction is by neutral PCNHCP cobalt(I) pincer complex proceeds via π-allyl mechanism. occurs readily at 80–90 °C, it compatible with wide variety functional groups. situ formed enamines could additionally be used one-pot inverse-electron-demand Diels–Alder to furnish series diversely substituted heterobiaryls, which further discussed this report.
Язык: Английский
Процитировано
2
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(45)
Опубликована: Июль 17, 2024
1,2-Diamination of alkenes represents an attractive way to generate differentiated vicinal diamines, which are prevalent motifs in biologically active compounds and catalysts. However, existing methods usually limited scope produce diamines where one or both nitrogens protected, adding synthetic steps for deprotection further N-functionalization reach a desired target. Furthermore, the range amino groups that can be introduced at internal position is fairly limited. Here we describe 1,2-diamination styrenes directly installs free group terminal wide variety unprotected nitrogen nucleophiles (primary secondary alkyl aromatic amines, sulfoximines, N-heterocycles, ammonia surrogate) position. Two complementary sets conditions encompass electronically activated deactivated with diverse substitution patterns functional groups. Moreover, this strategy extended 1,2-aminothiolation styrenes.
Язык: Английский
Процитировано
2
Chem Catalysis, Год журнала: 2023, Номер 3(12), С. 100813 - 100813
Опубликована: Ноя. 14, 2023
Enamides are versatile building blocks in organic synthesis that give access to complex nitrogen-containing compounds. However, despite the interest these compounds, synthetic strategies enamides with carbon-centered chirality atre scarce. In this work, we report an efficient method for of a new class chiral trifluoromethylated stereogenic center from easily accessible allylic amines by effective chirality-transfer process. The gives excellent yields and diastereo- enantioselectivities. scope reaction is broad, various substituents functional groups tolerated. Furthermore, transformations were carried out trifluoromethylated, structures. For example, photocatalytic E/Z isomerization also presented.
Язык: Английский
Процитировано
5
Chemical and Pharmaceutical Bulletin, Год журнала: 2024, Номер 72(5), С. 432 - 453
Опубликована: Апрель 30, 2024
We have developed efficient synthetic reactions using enamines and enamides carrying oxygen atom substituent on nitrogen, such as N-alkoxyenamines, N,α-dialkoxyenamines, N-alkoxyanamides, N-(benzoyloxy)enamides. The umpolung reaction by polarity inversion at the β-position of N-alkoxyenamines afforded α-alkyl-, α-aryl-, α-alkenyl-, α-heteroarylketones aluminum reagent nucleophiles. Furthermore, one-pot α-phenylation ketones has been also developed. applied this method to N,α-dialkoxyenamine, generated from N-alkoxyamide afford α-arylamides. vicinal functionalization achieved with formation two new carbon–carbon bonds an organo-aluminum subsequent allyl magnesium bromide or tributyltin cyanide. A sequential retro-ene arylation for conversion N-alkoxyenamides corresponding tert-alkylamines. [3,3]-sigmatropic rearrangement N-(benzoyloxy)enamides followed cyclic β-aryl-β-amino alcohols bearing a tetrasubstituted carbon center. resulting products were converted into sterically congested β-amino alcohols, well dissociative anesthetic agent Tiletamine.
Язык: Английский
Процитировано
1
Organic Letters, Год журнала: 2024, Номер unknown
Опубликована: Сен. 23, 2024
Herein, we have developed a catalyst-free four-component carbosulfonylation of enamides involving indoles, DABCO·(SO
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(14), С. 10014 - 10019
Опубликована: Июль 7, 2023
The Spin-Center Shift (SCS) elimination is a specific way for the generation of radicals with relevance in synthetic and biochemical pathways. combination SCS-mediated radical chemistry atom-transfer addition (ATRA) offers new directions diversity-oriented chemical synthesis. Herein, we report photoredox three-component reaction α-acyloxy-N-heterocycles as precursors, styrene derivatives trapping agents, alcohols nucleophilic quenchers. novel radical-polar crossover provides access to diverse set branched ethers possessing high structural complexity. utility transformation was also demonstrated by synthesis complex drug derivative it easily scalable multigram level. scope limitations were explored plausible mechanism proposed.
Язык: Английский
Процитировано
2
Catalysts, Год журнала: 2023, Номер 13(6), С. 919 - 919
Опубликована: Май 23, 2023
A new and powerful visible-light-induced difunctionalization of the C-C σ-bond alkylidenecyclopropanes via a ring-opening process was developed. Importantly, acyl chlorides are used as both Cl sources. This strategy provides an effective route for bond with radical Cl− to construct C-Cl in one pot. In addition, it has wide range substrates can tolerate various functional groups.
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(20), С. 14487 - 14493
Опубликована: Сен. 28, 2023
Methyl substitution at the double bond of N-alkenyl anilides influences both preferred conformation and susceptibility to acidic hydrolysis. The R1-substituted amide favors trans conformation, whereas amides substituted R2 or R3 favor cis conformation. Substitution R1 positions increases ratio conformer. DFT study indicated that these conformational preferences can be explained in terms substituent-induced torsion twisting moiety relative plane. enhances hydrolysis, stability. effect on was showcased by contrasting anilide (trans) hydrogenated N-isopropyl (cis).
Язык: Английский
Процитировано
1
Angewandte Chemie, Год журнала: 2024, Номер 136(45)
Опубликована: Июль 17, 2024
Abstract 1,2‐Diamination of alkenes represents an attractive way to generate differentiated vicinal diamines, which are prevalent motifs in biologically active compounds and catalysts. However, existing methods usually limited scope produce diamines where one or both nitrogens protected, adding synthetic steps for deprotection further N‐functionalization reach a desired target. Furthermore, the range amino groups that can be introduced at internal position is fairly limited. Here we describe 1,2‐diamination styrenes directly installs free group terminal wide variety unprotected nitrogen nucleophiles (primary secondary alkyl aromatic amines, sulfoximines, N ‐heterocycles, ammonia surrogate) position. Two complementary sets conditions encompass electronically activated deactivated with diverse substitution patterns functional groups. Moreover, this strategy extended 1,2‐aminothiolation styrenes.
Язык: Английский
Процитировано
0