Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(1), С. 100 - 105
Опубликована: Ноя. 14, 2023
A [4 + 2] cyclization reaction of N -allenylsulfonamides and enaminones towards unsymmetrical 1,4-dihydropyridine sulfones with a 1,3-sulfonyl shift was reported simple operation for diversification also achieved.
Язык: Английский
Chinese Chemical Letters, Год журнала: 2024, Номер 35(9), С. 109494 - 109494
Опубликована: Янв. 6, 2024
Язык: Английский
Процитировано
7
ACS Catalysis, Год журнала: 2024, Номер 14(10), С. 7814 - 7845
Опубликована: Май 6, 2024
Because of its wide applicability in the synthesis diverse unsaturated building blocks, allene–alkyne (AA) coupling has emerged as a powerful methodology to drive useful chemical transformations past two decades. Considering recent discoveries this active research area, Review, we aim support chemists selection suitable methods, particularly intermolecular approaches, according needs. However, inherent similarities between reactivities π-systems create considerable obstacles while predicting selectivity an platform. Therefore, herein, couplings for chemoselective, stereoselective, and regioselective syntheses acyclic cyclic C-skeletons are reviewed. considering lack well-organized review field, initially provide brief historical overview types thermally induced reactions that mostly feasible electronically biased components nonselective. Subsequently, emerging selective strategies described, which include activator-controlled neighboring functional group-assisted regio-, stereo-, π-skeleton-divergent processes. Overall, Review is divided into parts. In first part, fabrication explained reaction types. second synthetic affording structures reviewed based on substrate class (that is, nonassisted assisted substrates). Key intermediates each subset factors affecting product-selective discrimination species with highlight rationale systemically summarized. Understanding these structure- catalyst-dependent provides insights regulation chemoselectivities title AA cross-couplings and, therefore, design alternative catalytic routes distinct mechanistic features.
Язык: Английский
Процитировано
7
Chinese Journal of Chemistry, Год журнала: 2022, Номер 40(15), С. 1767 - 1776
Опубликована: Апрель 20, 2022
Comprehensive Summary Developing reactions for the synthesis of 6‐6‐4 and 6‐4 carbocyclic scaffolds with a chiral quaternary center at bridgehead position is highly desired, considering existence such skeletons in natural products biological activities potential using these molecules downstream studies chemical biology medicinal chemistry. Report here accessing target high chemo‐, regio‐ enantio‐selectivities through Pd(II)/chiral N , ’‐disulfonyl bisimidazoline (Bim) ligand‐catalyzed asymmetric reaction yne‐allenones arylboronic acids. Realization skeleton ring‐junction all‐carbon stereocenter one‐step process while synthesizing two‐step process, which begins intramolecular [2 + 2] allenes alkynes, followed by Pd‐catalyzed addition acids to cyclic enones generated first step. Noteworthy that Bim ligand as C 2 ‐symmetric ’‐bidentateanionic ligand, designed us, coordinating Pd catalyst was applied catalyze 1,4‐conjugate catalytic performance (the can be carried out air). DFT calculations have been understand how take place, origins enantioselectivity, relative reactivities different substrates.
Язык: Английский
Процитировано
23
Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(9), С. 1332 - 1384
Опубликована: Март 14, 2023
Abstract Conjugated and non‐conjugated allenones appear as recurring motifs in organic synthesis, natural products mechanistic investigations showing unique properties applications. The ability of to build cycles has provided a direct access strained systems, medium‐sized rings, arenes, heterocycles complex polycycles. In addition, have served models catalysis. critic compilation herein presented will provide an exhaustive overview the synthetic possibilities may offer, which certainly inspire our community their search more efficient methodologies, preparation biological pharmaceutical targets, improve knowledge theoretical chemistry. Great part this review discuss aspects, catalysis innovation insights chemical transformations implying allenone motif. many examples on total synthesis pharmacologically active compounds be described. We hope that attractive chemistry, catalysis, medicinal chemistry communities. magnified image
Язык: Английский
Процитировано
16
Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(9), С. 2477 - 2484
Опубликована: Янв. 1, 2024
A variety of optically active tertiary propargylic alcohols and tetrasubstituted 2,3-allenoic acids have been synthesized via a Pd(( R )-DTBM-SEGphos)Cl 2 -catalyzed carboxylative kinetic resolution reaction racemic alcohols.
Язык: Английский
Процитировано
5
Chinese Chemical Letters, Год журнала: 2022, Номер 34(4), С. 107751 - 107751
Опубликована: Авг. 23, 2022
Язык: Английский
Процитировано
19
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(4), С. 2057 - 2068
Опубликована: Янв. 30, 2023
This study describes a visible-light-induced cascade reaction for preparing cyanoalkyl-containing polyheterocycles initiated by the photoinduced radical addition of N-arylacrylamide derivatives using cyclic oxime esters as sources followed cyanoalkyl-mediated cyclization. protocol features outstanding functional group compatibility, providing variety desired phenanthridine in moderate to good yields. Moreover, application microflow technique enhanced these reactions compared with equivalent batch reaction, significantly reducing times 10 min.
Язык: Английский
Процитировано
13
Organic Letters, Год журнала: 2023, Номер 25(20), С. 3713 - 3717
Опубликована: Май 15, 2023
DBU-catalyzed spiro-annulation and concomitant ring expansion/domino reaction of δ-acetoxy allenoates with cycl-2-ene-N-sulfonyl hydrazides afford ring-expanded (5 → 6, 6 7, 7 8) products. By contrast, cycl-3-ene/ane-N-sulfonyl hydrazones under similar conditions deliver pyrazole cores the same allenoate that involves allylic elimination in which serves as 3C-synthon. The key spirocyclic intermediates, well dienyl-amine are isolated characterized. An extension to (R)-(-)-carvone-derived sulfonyl hydrazide also led expansion gave pyrazoloazepine.
Язык: Английский
Процитировано
12
Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(16), С. 1987 - 1993
Опубликована: Апрель 7, 2023
Comprehensive Summary Metallacyclopentadienes play a vital role in transition‐metal mediated and catalyzed cycloaddition reactions of alkynes. Though versatile metallacyclopentadienes with alkynes have been disclosed, [2+1] cycloadditions never discovered. In present work, we report the formal metallacyclopentadiene unit broad scope commercial alkynes, providing facile strategy to construct tetracyclic conjugated compounds. The deuterated experiment indicates metal vinylidene intermediate has involved cycloaddition. Moreover, electrophilic substitution reaction compound aid density functional theory (DFT) calculated Fukui functions is investigated. These compounds exhibit absorption spectra whole visible region which could be employed as potential photovoltaic materials.
Язык: Английский
Процитировано
11
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(17), С. 12432 - 12444
Опубликована: Авг. 21, 2023
A DMAP-catalyzed sequential benzannulation and lactonization strategy in which δ-acetoxy allenoate functions as a 5C-synthon its reaction with cyclic sulfamidate imines is reported. This platform delivers π-extended coumarin frameworks under metal-free conditions via allylic elimination followed by Mannich coupling, proton shifts, C-N bond cleavage, key steps. The driving force for this domino the formation of diene-ammonium intermediate O-S cleavage. ESI-HRMS has been useful gaining insights into pathway.
Язык: Английский
Процитировано
11