Nature, Journal Year: 2023, Volume and Issue: 623(7985), P. 66 - 70
Published: Sept. 20, 2023
Language: Английский
Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)
Published: Feb. 1, 2024
Macrolactones exhibit distinct conformational and configurational properties are widely found in natural products, medicines, agrochemicals. Up to now, the major effort for macrolactonization is directed toward identifying suitable carboxylic acid/alcohol coupling reagents address challenges associated with macrocyclization, wherein stereochemistry of products usually controlled by substrate's inherent chirality. It remains largely unexplored using catalysts govern both macrolactone formation stereochemical control. Here, we disclose a non-enzymatic organocatalytic approach construct macrolactones bearing chiral planes from achiral substrates. Our strategy utilizes N-heterocyclic carbene (NHC) as potent acylation catalyst that simultaneously mediates macrocyclization controls planar chirality during catalytic process. varying ring sizes sixteen twenty members obtained good-to-excellent yields enantiomeric ratios. study shall open new avenues accessing various stereogenic elements structures readily available small-molecule catalysts.
Language: Английский
Citations
21
Chem, Journal Year: 2024, Volume and Issue: 10(5), P. 1541 - 1552
Published: March 15, 2024
Language: Английский
Citations
20
Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)
Published: Jan. 12, 2024
Abstract We report an organocatalyst that combines a triazolium N-heterocyclic carbene (NHC) with squaramide as hydrogen-bonding donor (HBD), which can effectively catalyze the atroposelective ring-opening of biaryl lactams via unique amide C–N bond cleavage mode. The free species attacks carbonyl, forming axially chiral acyl-azolium intermediate. Various amines be accessed by this methodology up to 99% ee and yield. By using mercaptan catalyst turnover agent, resulting thioester synthon transformed into several interesting atropisomers. Both control experiments theoretical calculations reveal crucial role hybrid NHC-HBD skeleton, activates H-bonding brings it spatially close centre. This discovery illustrates potential chimera demonstrates complementary strategy for activation manipulation.
Language: Английский
Citations
17
Coordination Chemistry Reviews, Journal Year: 2024, Volume and Issue: 514, P. 215941 - 215941
Published: May 18, 2024
Language: Английский
Citations
16
Chemical Communications, Journal Year: 2022, Volume and Issue: 58(95), P. 13188 - 13197
Published: Jan. 1, 2022
Improved stability and higher degree of synthetic tunability has allowed N-heterocyclic carbenes to supplant thiols as ligands for gold surface functionalization. This review article summarizes the basic science applications NHCs on gold.
Language: Английский
Citations
57
ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(5), P. 3111 - 3137
Published: Feb. 21, 2022
Cobalt–N-heterocyclic carbene (NHC) complexes have emerged as an attractive class of 3d transition metal catalysts for a broad range chemical processes, including cross-coupling, hydrogenation, hydrofunctionalization, and cycloaddition reactions. Herein, we present comprehensive review catalytic methods utilizing cobalt–NHC with focus on the catalyst structure, role NHC ligand, properties system, mechanism, synthetic utility. The survey clearly suggests that recent emergence well-defined may tremendous utility in design application reactions using more abundant metals.
Language: Английский
Citations
56
Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)
Published: April 1, 2022
Abstract A catalytic method for the enantioselective and C4-selective functionalization of pyridine derivatives is yet to be developed. Herein, we report an efficient asymmetric β-pyridylations enals that involve N-heterocyclic carbene (NHC) catalysis with excellent control over enantioselectivity pyridyl C4-selectivity. The key strategy precise stereocontrol involves enhancing interactions between chiral NHC-bound homoenolate pyridinium salt in presence hexafluorobenzene, which effectively differentiates two faces radical. Room temperature sufficient this transformation, reaction efficiency further accelerated by photo-mediation. This methodology exhibits broad functional group tolerance enables facile access a diverse range enantioenriched β-pyridyl carbonyl compounds under mild metal-free conditions.
Language: Английский
Citations
50
Science China Chemistry, Journal Year: 2022, Volume and Issue: 65(10), P. 1938 - 1944
Published: Sept. 2, 2022
Language: Английский
Citations
42
Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(34), P. 15431 - 15436
Published: Aug. 17, 2022
Heterogeneous palladium catalysts modified by N-heterocyclic carbenes (NHCs) are shown to be highly effective toward the direct synthesis of hydrogen peroxide (H
Language: Английский
Citations
41
Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 29(4)
Published: Oct. 7, 2022
N-Heterocyclic carbene (NHC) catalysis is a by now consolidated organocatalytic platform for number of synthetic (asymmetric) transformations via diverse reaction modes/intermediates. In addition to the typical umpolung processes involving acyl anion/homoenolate equivalent species, implementation protocols under oxidative conditions greatly expands possibilities this methodology. Oxidative NHC-catalysis allows and oxygenative through specific manipulations Breslow-type species depending upon oxidant used (external or O
Language: Английский
Citations
39