Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)
Published: April 3, 2025
Language: Английский
Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(13), P. 1487 - 1492
Published: March 10, 2024
Comprehensive Summary We report herein an unprecedented N ‐heterocyclic carbene‐catalyzed formal [3 + 3] annulation of ynals with ‐Ts indolin‐3‐ones under the oxidation condition affording functionalized pyrano[3,2‐ b ]indol‐2‐ones. The alkynyl acylazoliums via combination a carbene in presence oxidate proved to be important intermediates for success this transformation. This method features broad substrate scope and mild conditions, including axially chiral skeletons suitable substitutions.
Language: Английский
Citations
9
Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)
Published: April 10, 2024
Abstract Planar chiral [2.2]paracyclophanes consist of two functionalized benzene rings connected by ethylene bridges. These organic compounds have a wide range applications in asymmetric synthesis, as both ligands and catalysts, materials science, polymers, energy dyes. However, these molecules can only be accessed enantiomer separation via (a) time-consuming separations (b) kinetic resolution approaches, often with limited substrate scope, yielding enantiomers. Here, we report simple, efficient, metal-free protocol for organocatalytic desymmetrization prochiral diformyl[2.2]paracyclophanes. Our detailed experimental mechanistic study highlights differences the origin enantiocontrol pseudo - para pseudo-gem diformyl derivatives NHC catalyzed desymmetrizations based on whether key Breslow intermediate is irreversibly or reversibly formed this process. This gram-scale reaction enables follow-up derivatizations carbonyl groups, producing various enantiomerically pure planar [2.2]paracyclophane derivatives, thereby underscoring potential method.
Language: Английский
Citations
9
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 24, 2025
An N-heterocyclic carbene-catalyzed atroposelective [3 + 3] annulation of alkynyl acylazoliums with benzothiazole derivatives has been developed for the divergent synthesis axially chiral triaryl 2-pyranones and fused 2-pyridones. The regioselectivity this protocol depends on structure benzothiazoles three different nucleophilic centers. obtained frameworks represent a new class arylheterocycle atropisomers, which may be potentially useful in medicinal chemistry.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 28, 2025
The in situ-generated pyrrolin-3-ones serve as novel and versatile synthons, being employed intermediates for the efficient production of pyrrole-fused lactones with high yield excellent enantioselectivity. Herein, we introduce emerging rhodium oxidative N-heterocyclic carbene relay catalysis that enables a highly enantioselective cascade annulation between easily available 1,2,3-triazoles enals. In this proof-of-concept study, engage α,β-unsaturated acylazolium generated from enals via catalysis.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2024, Volume and Issue: 26(3), P. 702 - 707
Published: Jan. 11, 2024
We report herein an efficient NHC-catalyzed kinetic resolution of acyclic tertiary propargylic alcohols that provides them in high to excellent enantioselectivity. This is the first example realized by enantioselective acylation. The recovered enantioenriched can be facilely converted into other valuable compounds such as densely functionalized and carbmates yields stereopurity. Density functional theory calculations were performed determine reaction mechanism understand origin enantiodiscrimination.
Language: Английский
Citations
5
Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 917 - 921
Published: Jan. 18, 2024
A chiral carbene-catalyzed chemo- and enantioselective reaction with racemic biaryl aldehydes α-bromoenals is developed for access to axially 2-arylbenzaldehydes through atroposelective dynamic kinetic resolution (DKR) processes. This DKR strategy can tolerate a broad scope of substrates diverse functionalities. The 2-aryl benzaldehyde products generally afford moderate good yields enantioselectivities. molecules afforded from the current approach are variable simple transformations functional excellent optical purities.
Language: Английский
Citations
5
Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(9)
Published: March 7, 2024
N-Heterocyclic carbenes (NHCs) catalysts have been employed as effective tools in the development of various reactions, which made notable contributions developing diverse reaction modes and generating significant functionalized molecules. This review provides an overview recent advancements chemo- regioselective activation different aldehydes using NHCs, categorized into five parts based on modes. A brief conclusion outlook is provided to stimulate novel for accessing functional
Language: Английский
Citations
5
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(12), P. 3308 - 3319
Published: Jan. 1, 2024
An unprecedented ligand-enabled stereodivergent construction of both N–N axial and point chirality in a single step is reported.
Language: Английский
Citations
5
Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(7), P. 2199 - 2205
Published: May 28, 2024
Language: Английский
Citations
5
Organic Letters, Journal Year: 2024, Volume and Issue: 26(8), P. 1584 - 1588
Published: Feb. 20, 2024
We have developed a catalytic method using chiral N-heterocyclic carbene (NHC) as the sole organic catalyst to synthesize planar carbonitriles asymmetrically, resulting in optically pure, multifunctional compounds. The demonstrates remarkable tolerance toward diverse substituents and substitution patterns through kinetic resolution (KR) or desymmetrization processes. pure products hold significant potential for applications asymmetric synthesis antibacterial pesticide development.
Language: Английский
Citations
4